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

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

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 C...

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Veröffentlicht in:Angewandte Chemie International Edition 2003-07, Vol.42 (28), p.3274-3278
Hauptverfasser: Aggarwal, Varinder K., Bae, Imhyuck, Lee, Hee-Yoon, Richardson, Jeffery, Williams, David T.
Format: Artikel
Sprache:eng
Schlagworte:
asymmetric synthesis
epoxidation
sulfur
synthetic methods
ylides
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Beschreibung
Zusammenfassung: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. R1, R2=hydrogen, alkyl, alkenyl, alkynyl, aryl, or pyridyl.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200350968