{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,27]],"date-time":"2026-01-27T07:42:47Z","timestamp":1769499767941,"version":"3.49.0"},"reference-count":75,"publisher":"Wiley","issue":"2","license":[{"start":{"date-parts":[[2012,12,3]],"date-time":"2012-12-03T00:00:00Z","timestamp":1354492800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry \u0097 An Asian Journal"],"published-print":{"date-parts":[[2013,2]]},"DOI":"10.1002\/asia.201201021","type":"journal-article","created":{"date-parts":[[2012,12,3]],"date-time":"2012-12-03T13:45:12Z","timestamp":1354542312000},"page":"354-358","source":"Crossref","is-referenced-by-count":33,"title":["Direct Catalytic Asymmetric Addition of Allylic Cyanides to Aldehydes for Expeditious Access to Enantioenriched Unsaturated \u03b4\u2010Valerolactones"],"prefix":"10.1002","volume":"8","author":[{"given":"Yasunari","family":"Otsuka","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hisashi","family":"Takada","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Shigeo","family":"Yasuda","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Naoya","family":"Kumagai","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Masakatsu","family":"Shibasaki","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2012,12,3]]},"reference":[{"key":"e_1_2_3_1_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1962206"},{"key":"e_1_2_3_2_2","unstructured":"The catalytic asymmetric direct aldol reaction represents this C\uf8ffC bond\u2010forming strategy. For reviews of direct catalytic asymmetric aldol reactions see:"},{"key":"e_1_2_3_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/1099-0690(200205)2002:10<1595::AID-EJOC1595>3.0.CO;2-M"},{"key":"e_1_2_3_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar0300468"},{"key":"e_1_2_3_5_2","volume-title":"Modern Aldol Reactions","year":"2004"},{"key":"e_1_2_3_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr0684016"},{"key":"e_1_2_3_7_2","doi-asserted-by":"publisher","DOI":"10.1039\/b923537j"},{"key":"e_1_2_3_8_2","unstructured":"Recent reviews on cooperative catalysis see: Lewis acid\/Br\u00f8nsted base"},{"key":"e_1_2_3_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr010297z"},{"key":"e_1_2_3_10_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201100918"},{"key":"e_1_2_3_10_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201100918"},{"key":"e_1_2_3_11_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-2005-869831"},{"key":"e_1_2_3_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar700261a"},{"key":"e_1_2_3_13_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200460394"},{"key":"e_1_2_3_13_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200460394"},{"key":"e_1_2_3_14_2","volume-title":"Acid Catalysis in Modern Organic Synthesis","author":"Yamamoto H.","year":"2008"},{"key":"e_1_2_3_15_2","unstructured":"For selected examples of direct catalytic asymmetric addition of high\u2010pKacarbon nucleophiles: alkylnitriles see:"},{"key":"e_1_2_3_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol051423e"},{"key":"e_1_2_3_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja061221t"},{"key":"e_1_2_3_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja108764d"},{"key":"e_1_2_3_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja909758e"},{"key":"e_1_2_3_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja904575e"},{"key":"e_1_2_3_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja035509j"},{"key":"e_1_2_3_22_2","unstructured":"\u00a0"},{"key":"e_1_2_3_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja806572b"},{"key":"e_1_2_3_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja900001u"},{"key":"e_1_2_3_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja101687p"},{"key":"e_1_2_3_26_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201102467"},{"key":"e_1_2_3_26_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201102467"},{"key":"e_1_2_3_27_2","unstructured":"Examples for direct addition of allylic cyanides as pronucleophiles in racemic reaction systems see:"},{"key":"e_1_2_3_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo0106492"},{"key":"e_1_2_3_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol801070n"},{"key":"e_1_2_3_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja8000216"},{"key":"e_1_2_3_31_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201108795"},{"key":"e_1_2_3_31_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201108795"},{"key":"e_1_2_3_31_4","first-page":"12120","volume":"124","author":"Denmark S. E.","year":"2012","journal-title":"Angew. Chem."},{"key":"e_1_2_3_31_5","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201202139"},{"key":"e_1_2_3_32_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200600570"},{"key":"e_1_2_3_33_2","unstructured":"Isolation:"},{"key":"e_1_2_3_34_2","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.36.1595"},{"key":"e_1_2_3_35_2","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.36.1601"},{"key":"e_1_2_3_36_2","doi-asserted-by":"publisher","DOI":"10.1097\/00001813-199706000-00001"},{"key":"e_1_2_3_37_2","doi-asserted-by":"publisher","DOI":"10.1016\/0277-5379(86)90057-X"},{"key":"e_1_2_3_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo962166h"},{"key":"e_1_2_3_39_2","unstructured":"Total synthesis of fostriecin see:"},{"key":"e_1_2_3_40_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja010195q"},{"key":"e_1_2_3_41_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20011001)113:19<3779::AID-ANGE3779>3.0.CO;2-C"},{"key":"e_1_2_3_41_3","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20011001)40:19<3667::AID-ANIE3667>3.0.CO;2-6"},{"key":"e_1_2_3_42_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol025537r"},{"key":"e_1_2_3_43_2","doi-asserted-by":"publisher","DOI":"10.1039\/b201302a"},{"key":"e_1_2_3_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja030133v"},{"key":"e_1_2_3_45_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol020193q"},{"key":"e_1_2_3_46_2","doi-asserted-by":"publisher","DOI":"10.1039\/b209742g"},{"key":"e_1_2_3_47_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol027528o"},{"key":"e_1_2_3_48_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja042435i"},{"key":"e_1_2_3_49_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0562043"},{"key":"e_1_2_3_50_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2006.03.116"},{"key":"e_1_2_3_51_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol902365n"},{"key":"e_1_2_3_52_2","doi-asserted-by":"publisher","DOI":"10.1039\/b912267b"},{"key":"e_1_2_3_53_2","first-page":"2935","author":"Shibahara S.","year":"2009","journal-title":"Synthesis"},{"key":"e_1_2_3_54_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol101340n"},{"key":"e_1_2_3_55_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201000795"},{"key":"e_1_2_3_56_2","first-page":"3325","author":"Li D.","year":"2010","journal-title":"Synthesis"},{"key":"e_1_2_3_57_2","unstructured":"Absolute configuration of9\u2009bawas determined after ozonolysis of the double bond. See the Supporting Information for details."},{"key":"e_1_2_3_58_2","unstructured":"A preliminary result using \u03b3\u2010substituted allyl cyanide1\u2009bas a pronucleophile was shown in the following: A retarded reaction was observed and the use of phosphine oxide7at higher temperature (\u221220\u2009\u00b0C) was essential to promote the reaction. \u03b3\/\u03b1\u2010Selectivity and enantioselectivity need further studies for improvement."},{"key":"e_1_2_3_59_2","unstructured":"Attempted isolation of9\u2009garesulted inE\/Zisomerization."},{"key":"e_1_2_3_60_2","unstructured":"See the Supporting Information for details."},{"key":"e_1_2_3_61_2","unstructured":"\u00a0"},{"key":"e_1_2_3_62_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja001643h"},{"key":"e_1_2_3_63_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)02039-6"},{"key":"e_1_2_3_64_2","unstructured":"\u00a0"},{"key":"e_1_2_3_65_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00170a070"},{"key":"e_1_2_3_66_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00019a027"},{"key":"e_1_2_3_67_2","unstructured":"Each diastereomer of19has a quite similar1H\u2005NMR spectral pattern. A small aliquot of the diastereomeric mixture of19was converted into the corresponding benzoate for the determination of diastereomeric ratio by1H\u2005NMR spectroscopy. See the Supporting Information for details."},{"key":"e_1_2_3_68_2","unstructured":"The mismatchedR\u2010catalyst provided preferentially formed undesired diastereomer (4S 7R)."}],"container-title":["Chemistry \u2013 An Asian Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fasia.201201021","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/aces.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/asia.201201021","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,8]],"date-time":"2025-10-08T14:45:37Z","timestamp":1759934737000},"score":1,"resource":{"primary":{"URL":"https:\/\/aces.onlinelibrary.wiley.com\/doi\/10.1002\/asia.201201021"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2012,12,3]]},"references-count":75,"journal-issue":{"issue":"2","published-print":{"date-parts":[[2013,2]]}},"alternative-id":["10.1002\/asia.201201021"],"URL":"https:\/\/doi.org\/10.1002\/asia.201201021","archive":["Portico"],"relation":{},"ISSN":["1861-4728","1861-471X"],"issn-type":[{"value":"1861-4728","type":"print"},{"value":"1861-471X","type":"electronic"}],"subject":[],"published":{"date-parts":[[2012,12,3]]}}}