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Sulfur‐Ylide‐Mediated Synthesis of Functionalized and Trisubstituted Epoxides with High Enantioselectivity; Application to the Synthesis of CDP‐840
Author(s) -
Aggarwal Varinder K.,
Bae Imhyuck,
Lee HeeYoon,
Richardson Jeffery,
Williams David T.
Publication year - 2003
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200350968
Subject(s) - sulfonium , ylide , chemistry , aryl , sulfur , alkyl , combinatorial chemistry , organic chemistry , salt (chemistry)
Benzyl and substituted allyl sulfonium salts react with a broad range of simple and functionalized aldehydes and ketones to give epoxides with high diastereoselectivity and high enantioselectivity (see scheme). The process has been applied to a short synthesis of the phosphodiesterase‐IV inhibitor CDP‐840. R 1 , R 2 =hydrogen, alkyl, alkenyl, alkynyl, aryl, or pyridyl.