{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,7]],"date-time":"2026-10-07T19:36:45Z","timestamp":1791401805851,"version":"4.3.3"},"reference-count":140,"publisher":"Wiley","issue":"35","license":[{"start":{"date-parts":[[2013,7,23]],"date-time":"2013-07-23T00:00:00Z","timestamp":1374537600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2013,8,26]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>A directed cross\u2010aldol reaction of silyl enol ethers with carbonyl compounds, such as aldehydes and ketones, promoted by a Lewis acid, a reaction which is now widely known as the Mukaiyama aldol reaction. It was first reported in 1973, and this year marks the 40th anniversary. The directed cross\u2010aldol reactions mediated by boron enolates and tin(II) enolates also emerged from the Mukaiyama laboratory. These directed cross\u2010aldol reactions have become invaluable tools for the construction of stereochemically complex molecules from two carbonyl compounds. This Minireview provides a succinct historical overview of their discoveries and the early stages of their development.<\/jats:p>","DOI":"10.1002\/anie.201303192","type":"journal-article","created":{"date-parts":[[2013,7,24]],"date-time":"2013-07-24T13:59:12Z","timestamp":1374674352000},"page":"9109-9118","source":"Crossref","is-referenced-by-count":304,"title":["The Mukaiyama Aldol Reaction: 40\u2005Years of Continuous Development"],"prefix":"10.1002","volume":"52","author":[{"given":"Jun\u2010ichi","family":"Matsuo","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Masahiro","family":"Murakami","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2013,7,23]]},"reference":[{"key":"e_1_2_9_1_2","unstructured":"\u00a0"},{"key":"e_1_2_9_2_2","first-page":"1","volume":"16","author":"Nielsen A. T.","year":"1968","journal-title":"Org. React."},{"key":"e_1_2_9_3_2","first-page":"203","volume":"28","author":"Mukaiyama T.","year":"1982","journal-title":"Org. React."},{"key":"e_1_2_9_4_2","unstructured":"\u00a0"},{"key":"e_1_2_9_5_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19630752007"},{"key":"e_1_2_9_5_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.196306831"},{"key":"e_1_2_9_6_2","doi-asserted-by":"publisher","DOI":"10.1002\/cber.19620951008"},{"key":"e_1_2_9_7_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1973.1011"},{"key":"e_1_2_9_8_2","unstructured":"Silyl enol ether is a conventional name. Alkenyl silyl ether alkenyloxysilane silyloxyalkene or silicon enolate would be more appropriate from the viewpoint of the nomenclature. In this review the term silyl enol ether is used because it has been recognized as the technical term for 45\u2005years since it appeared in the report by Stork and Hudrlik in 1968.[14]"},{"key":"e_1_2_9_9_2","doi-asserted-by":"publisher","DOI":"10.1002\/cber.19660990818"},{"key":"e_1_2_9_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00791a039"},{"key":"e_1_2_9_11_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)78044-0"},{"key":"e_1_2_9_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00365a095"},{"key":"e_1_2_9_13_2","unstructured":"Review:"},{"key":"e_1_2_9_14_2","first-page":"239","volume-title":"Comprehensive Organic Synthesis, Vol.\u20052","author":"Kim B. M.","year":"1991"},{"key":"e_1_2_9_15_2","first-page":"1","volume":"51","author":"Cowden C. J.","year":"1997","journal-title":"Org. React."},{"key":"e_1_2_9_16_2","first-page":"1","volume":"46","author":"Mukaiyama T.","year":"1994","journal-title":"Org. React."},{"key":"e_1_2_9_17_2","volume-title":"Modern Aldol Reactions, Vol.\u20051,2","year":"2004"},{"key":"e_1_2_9_18_2","unstructured":"\u00a0"},{"key":"e_1_2_9_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00784a079"},{"key":"e_1_2_9_20_2","doi-asserted-by":"publisher","DOI":"10.1246\/bcsj.46.1807"},{"key":"e_1_2_9_21_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19770891205"},{"key":"e_1_2_9_21_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.197708171"},{"key":"e_1_2_9_22_2","unstructured":"\u00a0"},{"key":"e_1_2_9_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01018a051"},{"key":"e_1_2_9_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01018a052"},{"key":"e_1_2_9_25_2","unstructured":"\u00a0"},{"key":"e_1_2_9_26_2","doi-asserted-by":"publisher","DOI":"10.1039\/c39720000741"},{"key":"e_1_2_9_27_2","doi-asserted-by":"publisher","DOI":"10.1039\/C39720000946"},{"key":"e_1_2_9_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00831a019"},{"key":"e_1_2_9_29_2","unstructured":"\u00a0"},{"key":"e_1_2_9_30_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1975.989"},{"key":"e_1_2_9_31_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1975.319"},{"key":"e_1_2_9_32_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1974.1223"},{"key":"e_1_2_9_33_2","doi-asserted-by":"publisher","DOI":"10.1016\/B978-0-08-052349-1.00042-1"},{"key":"e_1_2_9_34_2","unstructured":"\u00a0"},{"key":"e_1_2_9_35_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19850971025"},{"key":"e_1_2_9_35_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.198508741"},{"key":"e_1_2_9_36_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00306a045"},{"key":"e_1_2_9_37_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00529a062"},{"key":"e_1_2_9_38_2","unstructured":"\u00a0"},{"key":"e_1_2_9_39_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)81736-6"},{"key":"e_1_2_9_40_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)87496-2"},{"key":"e_1_2_9_41_2","unstructured":"\u00a0"},{"key":"e_1_2_9_42_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)86495-9"},{"key":"e_1_2_9_43_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00300a008"},{"key":"e_1_2_9_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00313a002"},{"key":"e_1_2_9_45_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00088a053"},{"key":"e_1_2_9_46_2","unstructured":"\u00a0"},{"key":"e_1_2_9_47_2","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4020(92)80024-A"},{"key":"e_1_2_9_48_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00083a005"},{"key":"e_1_2_9_49_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00114a041"},{"key":"e_1_2_9_50_2","doi-asserted-by":"publisher","DOI":"10.1039\/a705801b"},{"key":"e_1_2_9_51_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja3052975"},{"key":"e_1_2_9_52_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00446a049"},{"key":"e_1_2_9_53_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00155a003"},{"key":"e_1_2_9_54_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00398a047"},{"key":"e_1_2_9_55_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00355a039"},{"key":"e_1_2_9_56_2","unstructured":"\u00a0"},{"key":"e_1_2_9_57_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0693542"},{"key":"e_1_2_9_58_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja7102586"},{"key":"e_1_2_9_59_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja2066169"},{"key":"e_1_2_9_60_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)96636-5"},{"key":"e_1_2_9_61_2","unstructured":"T. Mukaiyama\u2019s personal communication."},{"key":"e_1_2_9_62_2","doi-asserted-by":"publisher","DOI":"10.1246\/bcsj.44.3215"},{"key":"e_1_2_9_63_2","unstructured":"\u00a0"},{"key":"e_1_2_9_64_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01023a070"},{"key":"e_1_2_9_65_2","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4039(70)80029-6"},{"key":"e_1_2_9_66_2","unstructured":"\u00a0"},{"key":"e_1_2_9_67_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1976.559"},{"key":"e_1_2_9_68_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1977.153"},{"key":"e_1_2_9_69_2","doi-asserted-by":"publisher","DOI":"10.1246\/bcsj.53.174"},{"key":"e_1_2_9_70_2","doi-asserted-by":"publisher","DOI":"10.1002\/jlac.197519750711"},{"key":"e_1_2_9_71_2","unstructured":"\u00a0"},{"key":"e_1_2_9_72_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00514a045"},{"key":"e_1_2_9_73_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)93682-2"},{"key":"e_1_2_9_74_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)93683-4"},{"key":"e_1_2_9_75_2","unstructured":"For transition states for the stereoselective formation ofE\u2010 andZ\u2010boron enolates see Ref.\u2005[9a]."},{"key":"e_1_2_9_76_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1980.1507"},{"key":"e_1_2_9_77_2","unstructured":"\u00a0"},{"key":"e_1_2_9_78_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1982.353"},{"key":"e_1_2_9_79_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1982.1903"},{"key":"e_1_2_9_80_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1982.1459"},{"key":"e_1_2_9_81_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2008.12.030"},{"key":"e_1_2_9_82_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00398a058"},{"key":"e_1_2_9_83_2","doi-asserted-by":"crossref","unstructured":"S.\u2005B.\u2005J. Kan K.\u2005K.\u2010H. Ng I. Paterson Angew. Chem.\u00ad2013 125 9267\u20139279;Angew. Chem. Int. Ed.\u00ad2013 \u00ad52 9097\u20139108.","DOI":"10.1002\/anie.201303914"},{"key":"e_1_2_9_84_2","unstructured":"\u00a0"},{"key":"e_1_2_9_85_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00286a036"},{"key":"e_1_2_9_86_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)85065-0"},{"key":"e_1_2_9_87_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00196a081"},{"key":"e_1_2_9_88_2","unstructured":"\u00a0"},{"key":"e_1_2_9_89_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1982.1441"},{"key":"e_1_2_9_90_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1983.297"},{"key":"e_1_2_9_91_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)82423-6"},{"key":"e_1_2_9_92_2","unstructured":"\u00a0"},{"key":"e_1_2_9_93_2","first-page":"824","author":"Reetz M. T.","year":"1986","journal-title":"Chem. Ind."},{"key":"e_1_2_9_94_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)85047-9"},{"key":"e_1_2_9_95_2","unstructured":"\u00a0"},{"key":"e_1_2_9_96_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1989.297"},{"key":"e_1_2_9_97_2","doi-asserted-by":"publisher","DOI":"10.1016\/0022-328X(90)85213-I"},{"key":"e_1_2_9_98_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00011a030"},{"key":"e_1_2_9_99_2","unstructured":"\u00a0"},{"key":"e_1_2_9_100_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1990.129"},{"key":"e_1_2_9_101_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1990.1455"},{"key":"e_1_2_9_102_2","unstructured":"\u00a0"},{"key":"e_1_2_9_103_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3765(19980710)4:7<1137::AID-CHEM1137>3.0.CO;2-Z"},{"key":"e_1_2_9_104_2","doi-asserted-by":"publisher","DOI":"10.1007\/978-3-642-58571-5_1"},{"key":"e_1_2_9_105_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr980415r"},{"key":"e_1_2_9_106_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3757(20000417)112:8<1406::AID-ANGE1406>3.0.CO;2-R"},{"key":"e_1_2_9_106_3","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3773(20000417)39:8<1352::AID-ANIE1352>3.0.CO;2-J"},{"key":"e_1_2_9_107_2","doi-asserted-by":"publisher","DOI":"10.1039\/B202901D"},{"key":"e_1_2_9_108_2","unstructured":"\u00a0"},{"key":"e_1_2_9_109_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1990.1015"},{"key":"e_1_2_9_110_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00098a065"},{"key":"e_1_2_9_111_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00113a031"},{"key":"e_1_2_9_112_2","unstructured":"\u00a0"},{"key":"e_1_2_9_113_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00003a047"},{"key":"e_1_2_9_114_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1991-20756"},{"key":"e_1_2_9_115_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00024a050"},{"key":"e_1_2_9_116_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)61236-4"},{"key":"e_1_2_9_117_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)60892-4"},{"key":"e_1_2_9_118_2","unstructured":"\u00a0"},{"key":"e_1_2_9_119_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja960712i"},{"key":"e_1_2_9_120_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja972547s"},{"key":"e_1_2_9_121_2","unstructured":"\u00a0"},{"key":"e_1_2_9_122_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00114a002"},{"key":"e_1_2_9_123_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja970900o"},{"key":"e_1_2_9_124_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja973331t"},{"key":"e_1_2_9_125_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja9943389"},{"key":"e_1_2_9_126_2","unstructured":"Direct in this case means the dispensation of preconversion of a carbonyl compound into a more reactive nucleophilic species:"},{"key":"e_1_2_9_127_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19971091716"},{"key":"e_1_2_9_127_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199718711"},{"key":"e_1_2_9_128_2","doi-asserted-by":"publisher","DOI":"10.1039\/b923537j"},{"key":"e_1_2_9_129_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201100918"},{"key":"e_1_2_9_129_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201100918"},{"key":"e_1_2_9_130_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201102423"},{"key":"e_1_2_9_130_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201102423"},{"key":"e_1_2_9_131_2","unstructured":"\u00a0"},{"key":"e_1_2_9_132_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar0300468"},{"key":"e_1_2_9_133_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr0684016"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fanie.201303192","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.201303192","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,10,16]],"date-time":"2023-10-16T20:20:58Z","timestamp":1697487658000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.201303192"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2013,7,23]]},"references-count":140,"journal-issue":{"issue":"35","published-print":{"date-parts":[[2013,8,26]]}},"alternative-id":["10.1002\/anie.201303192"],"URL":"https:\/\/doi.org\/10.1002\/anie.201303192","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2013,7,23]]}}}