Sulfur‐Ylide‐Mediated Synthesis of Functionalized and Trisubstituted Epoxides with High Enantioselectivity; Application to the Synthesis of CDP‐840 | Zendy

Aggarwal Varinder K. | Zendy; Bae Imhyuck | Zendy; Lee HeeYoon | Zendy; Richardson Jeffery | Zendy; Williams David T. | Zendy

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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.

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