{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,20]],"date-time":"2026-04-20T19:10:42Z","timestamp":1776712242498,"version":"3.51.2"},"reference-count":196,"publisher":"Pharmaceutical Society of Japan","issue":"1","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chem. Pharm. Bull.","CHEMICAL & PHARMACEUTICAL BULLETIN"],"published-print":{"date-parts":[[2011]]},"DOI":"10.1248\/cpb.59.1","type":"journal-article","created":{"date-parts":[[2011,1,4]],"date-time":"2011-01-04T06:10:04Z","timestamp":1294121404000},"page":"1-22","source":"Crossref","is-referenced-by-count":24,"title":["Development of Atom-Economical Catalytic Asymmetric Reactions under Proton Transfer Conditions: Construction of Tetrasubstituted Stereogenic Centers and Their Application to Therapeutics"],"prefix":"10.1248","volume":"59","author":[{"given":"Naoya","family":"Kumagai","sequence":"first","affiliation":[{"name":"The University of Tokyo"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"163","reference":[{"key":"1","unstructured":"1) “Comprehensive Asymmetric Catalysis,” ed. by Jacobsen E. 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U.S.A.<\/i>, 101<\/b>, 5363—5367 (2004).","DOI":"10.1073\/pnas.0307113101"},{"key":"66","doi-asserted-by":"crossref","unstructured":"66) For a recent review, see: Trost B. M., Jiang C., Synthesis<\/i>, 2006<\/b>, 369—396 (2006).","DOI":"10.1055\/s-2006-926302"},{"key":"67","unstructured":"67) For a review on α-cyanocarbanions, see: Arseniyadis S., Kyler K. S., Watt D. S., Org. React.<\/i>, 31<\/b>, 1—71 (1984)."},{"key":"68","doi-asserted-by":"publisher","unstructured":"68) For a review on α-cyanocarbanions, see: Fleming F. F., Shook B. C., Tetrahedron<\/i>, 58<\/b>, 1—23 (2002).","DOI":"10.1016\/S0040-4020(01)01134-6"},{"key":"69","doi-asserted-by":"crossref","unstructured":"69) For a review on α-cyanocarbanions, see: Fleming F. F., Iyer P. S., Synthesis<\/i>, 2006<\/b>, 893—913 (2006).","DOI":"10.1055\/s-2006-926363"},{"key":"70","doi-asserted-by":"crossref","unstructured":"70) For a recent review on direct Mannich reactions using unmodified pronucleophiles, see: Ting A., Schaus S. E., Eur. J. Org. Chem<\/i>., 2007<\/b>, 5797—5815 (2007), and references cited therein.","DOI":"10.1002\/ejoc.200700409"},{"key":"71","doi-asserted-by":"crossref","unstructured":"71) For a recent review on direct Mannich reactions using unmodified pronucleophiles, see: Verkade J. M. M., van Hemert L. J. C., Quaedflieg P. J. L. M., Rutjes F. P. J. T., Chem. Soc. Rev.<\/i>, 37<\/b>, 29—41 (2008).","DOI":"10.1039\/B713885G"},{"key":"72","unstructured":"72) For a general review on catalytic asymmetric Mannich reactions, see: Kobayashi S., Ueno M., “Comprehensive Asymmetric Catalysis,” Supplement 1, Chapter 29.5, ed. by Jacobsen E. N., Pfaltz A., Yamamoto H., Springer, Berlin, 2003, p. 143."},{"key":"73","doi-asserted-by":"publisher","unstructured":"73) For a general review on catalytic asymmetric Mannich reactions, see: Friestad G., Mathies A. K., Tetrahedron<\/i>, 63<\/b>, 2541—2569 (2007).","DOI":"10.1016\/j.tet.2006.11.076"},{"key":"74","doi-asserted-by":"crossref","unstructured":"74) Marigo M., Kjærsgaard A., Juhl K., Gathergood N., Jørgensen K. A., Chem. Eur. J.<\/i>, 9<\/b>, 2359—2367 (2003).","DOI":"10.1002\/chem.200204679"},{"key":"75","doi-asserted-by":"crossref","unstructured":"75) Hamashima Y., Sasamoto N., Hotta D., Somei H., Umebayashi N., Sodeoka M., Angew. Chem., Int. Ed.<\/i>, 44<\/b>, 1525—1529 (2005).","DOI":"10.1002\/anie.200462202"},{"key":"76","doi-asserted-by":"crossref","unstructured":"76) Ting A., Lou S., Schaus S. E., Org. Lett.<\/i>, 8<\/b>, 2003—2006 (2006).","DOI":"10.1021\/ol060304b"},{"key":"77","doi-asserted-by":"crossref","unstructured":"77) Tillman A. L., Ye J., Dixon D. J., Chem. Commun.<\/i>, 2006<\/b>, 1191—1193 (2006).","DOI":"10.1039\/b515725k"},{"key":"78","doi-asserted-by":"publisher","unstructured":"78) Yamaoka Y., Miyabe H., Yoshizumi Y., Takemoto Y., Synthesis<\/i>, 2007<\/b>, 2571—2575 (2007).","DOI":"10.1055\/s-2007-983795"},{"key":"79","doi-asserted-by":"crossref","unstructured":"79) Chen Z., Morimoto H., Matsunaga S., Shibasaki M., J. Am. Chem. Soc.<\/i>, 130<\/b>, 2170—2171 (2008).","DOI":"10.1021\/ja710398q"},{"key":"80","doi-asserted-by":"crossref","unstructured":"80) Nojiri A., Kumagai N., Shibasaki M., J. Am. Chem. Soc.<\/i>, 130<\/b>, 5630—5631 (2008).","DOI":"10.1021\/ja800326d"},{"key":"81","doi-asserted-by":"crossref","unstructured":"81) For a representative example of a Mannich-type reaction of 1,3-dicarbonyl compounds generating quaternary stereocenters displaying both syn<\/i>- and anti<\/i>-diastereoselectivity reported after our report, see: Hatano M., Horibe T., Ishihara K., J. Am. Chem. Soc.<\/i>, 132<\/b>, 56—57 (2010).","DOI":"10.1021\/ja909874b"},{"key":"82","doi-asserted-by":"crossref","unstructured":"82) For a representative example of a Mannich-type reaction of α-cyanoketones generating quaternary stereocenters reported after our report, see: Lee J. H., Kim D. Y., Adv. Synth. Catal.<\/i>, 351<\/b>, 1779—1782 (2009).","DOI":"10.1002\/adsc.200900268"},{"key":"83","doi-asserted-by":"crossref","unstructured":"83) Nojiri A., Kumagai N., Shibasaki M., J. Am. Chem. 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Commun.<\/i>, 2005<\/b>, 4450—4452 (2005).","DOI":"10.1039\/b505778g"},{"key":"129","doi-asserted-by":"publisher","unstructured":"129) For an example of catalytic chemoselective nucleophilic activation of alkylnitrile, see: Kumagai N., Matsunaga S., Shibasaki M., Tetrahedron<\/i>, 63<\/b>, 8598—8608 (2007).","DOI":"10.1016\/j.tet.2007.04.051"},{"key":"130","doi-asserted-by":"crossref","unstructured":"130) For an example of catalytic chemoselective nucleophilic activation of alkylnitrile, see: Goto A., Endo K., Ukai Y., Irle S., Saito S., Chem. Commun.<\/i>, 2008<\/b>, 2212—2214 (2008).","DOI":"10.1039\/b800634b"},{"key":"131","doi-asserted-by":"crossref","unstructured":"131) For an example of the use of allylic cyanides as pronucleophiles in racemic reactions, see: Kisanga P. B., Verkade J. G., J. Org. 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Catal.<\/i>, 349<\/b>, 759—764 (2007).","DOI":"10.1002\/adsc.200600405"},{"key":"140","doi-asserted-by":"crossref","unstructured":"140) Zhuang W., Saaby S., Jørgensen K. A., Angew. Chem., Int. Ed.<\/i>, 43<\/b>, 4476—4478 (2004).","DOI":"10.1002\/anie.200460158"},{"key":"141","doi-asserted-by":"publisher","unstructured":"141) For a review, see: Weinreb S. M., Orr R. K., Synthesis<\/i>, 2005<\/b>, 1205—1227 (2005).","DOI":"10.1055\/s-2005-865315"},{"key":"142","doi-asserted-by":"crossref","unstructured":"142) Yazaki R., Nitabaru T., Kumagai N., Shibasaki M., J. Am. Chem. Soc.<\/i>, 130<\/b>, 14477—14478 (2008).","DOI":"10.1021\/ja806572b"},{"key":"143","doi-asserted-by":"crossref","unstructured":"143) For a recent review of catalytic asymmetric synthesis of tertiary alcohols, see: Riant O., Hannedouche J., Org. Biomol. Chem.<\/i>, 5<\/b>, 873—888 (2007).","DOI":"10.1039\/b617746h"},{"key":"144","doi-asserted-by":"crossref","unstructured":"144) For a recent review of catalytic asymmetric synthesis of tertiary alcohols, see: Shibasaki M., Kanai M., Chem. Rev.<\/i>, 108<\/b>, 2853—2873 (2008).","DOI":"10.1021\/cr078340r"},{"key":"145","doi-asserted-by":"crossref","unstructured":"145) For a recent review of catalytic asymmetric synthesis of tertiary alcohols, see: Hatano M., Ishihara K., Synthesis<\/i>, 2008<\/b>, 1647—1675 (2008).","DOI":"10.1055\/s-2008-1067046"},{"key":"146","doi-asserted-by":"crossref","unstructured":"146) For a recent review of catalytic asymmetric synthesis of tertiary alcohols, see: Trost B. M., Weiss A. H., Adv. Synth. Catal.<\/i>, 351<\/b>, 963—983 (2009).","DOI":"10.1002\/adsc.200800776"},{"key":"147","doi-asserted-by":"crossref","unstructured":"147) For a recent review of catalytic asymmetric synthesis of tertiary alcohols, see: Adachi S., Harada T., Eur. J. Org. 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Ed.<\/i>, 45<\/b>, 1292—1297 (2006).","DOI":"10.1002\/anie.200503791"},{"key":"151","doi-asserted-by":"crossref","unstructured":"151) For an example of catalytic asymmetric addition to ketones coupled with hydrogenation, see: Komanduri V., Krische M. J., J. Am. Chem. Soc.<\/i>, 128<\/b>, 16448—16449 (2006).","DOI":"10.1021\/ja0673027"},{"key":"152","doi-asserted-by":"crossref","unstructured":"152) For an example of catalytic asymmetric addition to ketones coupled with hydrogenation, see: Shiomi T., Nishiyama H., Org. Lett.<\/i>, 9<\/b>, 1651—1654 (2007).","DOI":"10.1021\/ol070251d"},{"key":"153","doi-asserted-by":"crossref","unstructured":"153) For an example of catalytic asymmetric addition to ketones coupled with hydrogenation, see: Bower J. F., Kim I. S., Patman R. L., Krische M. J., Angew. Chem., Int. Ed.<\/i>, 48<\/b>, 34—46 (2009).","DOI":"10.1002\/anie.200802938"},{"key":"154","doi-asserted-by":"crossref","unstructured":"154) For an example of catalytic asymmetric addition to ketones coupled with hydrogenation, see: Chmura A., van der Kraan G. M., van Langen L. M., van Rantwijk F., Sheldon R. A., Adv. Synth. Catal.<\/i>, 348<\/b>, 1655—1661 (2006).","DOI":"10.1002\/adsc.200606140"},{"key":"155","doi-asserted-by":"crossref","unstructured":"155) von Langermann J., Mell A., Paetzold E., Daußmann T., Kragl U., Adv. Synth. Catal.<\/i>, 349<\/b>, 1418—1424 (2007).","DOI":"10.1002\/adsc.200700016"},{"key":"156","doi-asserted-by":"crossref","unstructured":"156) Zuend S. J., Jacobsen E. N., J. Am. Chem. Soc.<\/i>, 129<\/b>, 15872—15883 (2007).","DOI":"10.1021\/ja0735352"},{"key":"157","doi-asserted-by":"crossref","unstructured":"157) Yazaki R., Kumagai N., Shibasaki M., J. Am. Chem. Soc.<\/i>, 131<\/b>, 3195—3196 (2009).","DOI":"10.1021\/ja900001u"},{"key":"158","doi-asserted-by":"crossref","unstructured":"158) For a comprehensive review of Lewis base catalysis, see: Denmark S. E., Beutner G. L., Angew. Chem. Int. Ed.<\/i>, 47<\/b>, 1560—1638 (2008), and references cited therein.","DOI":"10.1002\/anie.200604943"},{"key":"159","doi-asserted-by":"crossref","unstructured":"159) For a selected example of Lewis base activation of a Brønsted base, see: McGrath M. J., O'Brien P., J. Am. Chem. Soc.<\/i>, 127<\/b>, 16378—16379 (2005).","DOI":"10.1021\/ja056026d"},{"key":"160","doi-asserted-by":"crossref","unstructured":"160) For a selected example of Lewis base activation of a Brønsted base, see: Saito S., Tsubogo T., Kobayashi S., J. Am. Chem. Soc.<\/i>, 129<\/b>, 5364—5365 (2007).","DOI":"10.1021\/ja0709730"},{"key":"161","doi-asserted-by":"crossref","unstructured":"161) For a selected example of Lewis base activation of a Brønsted base, see: Morimoto H., Yoshino T., Yukawa T., Lu G., Matsunaga S., Shibasaki M., Angew. Chem., Int. Ed.<\/i>, 47<\/b>, 9125—9129 (2008).","DOI":"10.1002\/anie.200803682"},{"key":"162","doi-asserted-by":"crossref","unstructured":"162) Enhanced Lewis basicity of LiOPh was observed by using bidentate phosphine oxide 25<\/b> in Mukaiyama aldol reactions. X-ray crystallographic analysis confirmed the coordination of 25<\/b> to Li cation in a bidentate fashion: Hatano M., Takagi E., Ishihara K., Org. Lett.<\/i>, 9<\/b>, 4527—4530 (2007).","DOI":"10.1021\/ol702052r"},{"key":"163","doi-asserted-by":"crossref","unstructured":"163) Yazaki R., Kumagai N., Shibasaki., J. Am. Chem. 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Chem.<\/i>, 226<\/b>, 209—215 (1982).","DOI":"10.1016\/S0022-328X(00)83404-X"},{"key":"167","doi-asserted-by":"crossref","unstructured":"167) For an aldol reaction using S<\/i>-silyl N<\/i>,S<\/i>-acetals, see: Goasdoue C., Goasdoue N., Gaudemar M., Tetrahedron Lett.<\/i>, 25<\/b>, 537—540 (1984).","DOI":"10.1016\/S0040-4039(00)99931-3"},{"key":"168","doi-asserted-by":"crossref","unstructured":"168) For a Mannich reaction using S<\/i>-silyl N<\/i>,S<\/i>-acetals, see: Goasdoue C., Gaudemar M., Tetrahedron Lett.<\/i>, 26<\/b>, 1015—1018 (1985).","DOI":"10.1016\/S0040-4039(00)98500-9"},{"key":"169","doi-asserted-by":"publisher","unstructured":"169) For an asymmetric aldol reaction mediated by a stoichiometric amount of a strong base and a chiral ligand, see: Iwasawa N., Yura T., Mukaiyama T., Tetrahedron<\/i>, 45<\/b>, 1197—1207 (1989).","DOI":"10.1016\/0040-4020(89)80028-6"},{"key":"170","doi-asserted-by":"crossref","unstructured":"170) Suzuki Y., Yazaki R., Kumagai N., Shibasaki M., Angew. Chem., Int. Ed.<\/i>, 48<\/b>, 5026—5029 (2009).","DOI":"10.1002\/anie.200901588"},{"key":"171","unstructured":"171) “Comprehensive Organic Synthesis,” Vol. 2, ed. by Trost B. M., Fleming I., Heathcock C.-H., Pergamon Press, Oxford, 1991."},{"key":"172","unstructured":"172) For a comprehensive review, see ref. 111."},{"key":"173","doi-asserted-by":"crossref","unstructured":"173) For a recent review of asymmetric aldol reactions, see: Palomo C., Oiarbide M., García J. M., Chem. Soc. Rev.<\/i>, 33<\/b>, 65—75 (2004).","DOI":"10.1039\/B202901D"},{"key":"174","doi-asserted-by":"publisher","unstructured":"174) For a recent review of asymmetric aldol reactions, see: Geary L. M., Hultin P. G., Tetrahedron: Asymmetry<\/i>, 20<\/b>, 131—173 (2009).","DOI":"10.1016\/j.tetasy.2008.12.030"},{"key":"175","unstructured":"175) For a recent review of direct catalytic asymmetric aldol reactions, see refs. 111—118."},{"key":"176","doi-asserted-by":"crossref","unstructured":"176) For a pioneering example of a direct catalytic asymmetric aldol reaction promoted by a metal-based catalyst, see: Yamada Y. M. A., Yoshikawa N., Sasai H., Shibasaki M., Angew. Chem., Int. Ed.<\/i>, 36<\/b>, 1871—1873 (1997).","DOI":"10.1002\/anie.199718711"},{"key":"177","doi-asserted-by":"crossref","unstructured":"177) For an early example of a direct aldol-type reaction using α-isocyanoacetate as an active methylene type aldol donor, see: Ito Y., Sawamura M., Hayashi T., J. Am. Chem. Soc.<\/i>, 108<\/b>, 6405—6406 (1986).","DOI":"10.1021\/ja00280a056"},{"key":"178","doi-asserted-by":"crossref","unstructured":"178) For a pioneering example of a direct catalytic asymmetric aldol reaction promoted by a metal-based catalyst, see: Yoshikawa N., Yamada Y. M. A., Das J., Sasai H., Shibasaki M., J. Am. Chem. Soc.<\/i>, 121<\/b>, 4168—4178 (1999).","DOI":"10.1021\/ja990031y"},{"key":"179","doi-asserted-by":"crossref","unstructured":"179) For a pioneering example of a direct catalytic asymmetric aldol reaction promoted by a metal-based catalyst, see: Trost B. M., Ito H., J. Am. Chem. Soc.<\/i>, 122<\/b>, 12003—12004 (2000).","DOI":"10.1021\/ja003033n"},{"key":"180","doi-asserted-by":"crossref","unstructured":"180) For a pioneering example of a direct catalytic asymmetric aldol reaction promoted by a metal-based catalyst, see: Mahrwald R., Ziemer B., Tetrahedron Lett.<\/i>, 43<\/b>, 4459—4461 (2002).","DOI":"10.1016\/S0040-4039(02)00822-5"},{"key":"181","doi-asserted-by":"crossref","unstructured":"181) For a pioneering example of a direct catalytic asymmetric intermolecular aldol reaction promoted by organocatalysts, see: List B., Lerner R. A., Barbas C. F. III, J. Am. Chem. Soc.<\/i>, 122<\/b>, 2395—2396 (2000).","DOI":"10.1021\/ja994280y"},{"key":"182","doi-asserted-by":"crossref","unstructured":"182) For a pioneering example of a direct catalytic asymmetric intermolecular aldol reaction promoted by organocatalysts, see: Sakthivel K., Notz W., Bui T., Barbas C. F. III, J. Am. Chem. Soc.<\/i>, 123<\/b>, 5260—5267 (2001).","DOI":"10.1021\/ja010037z"},{"key":"183","doi-asserted-by":"crossref","unstructured":"183) For a pioneering example of a direct catalytic asymmetric intermolecular aldol reaction promoted by organocatalysts, see: Saito S., Nakadai M., Yamamoto H., Synlett<\/i>, 2001<\/b>, 1245—1248 (2001).","DOI":"10.1055\/s-2001-16055"},{"key":"184","doi-asserted-by":"crossref","unstructured":"184) For direct catalytic asymmetric aldol (-type) reactions using aldol donors in the carboxylic acid oxidation state without electron-withdrawing α-substituents: alkylnitriles (up to 77% ee), see: Suto Y., Tsuji R., Kanai M., Shibasaki M., Org. 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