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Synthesis of novel C2-symmetrical chiral sulfides and their utility in asymmetric epoxidation of aldehydes

✍ Scribed by Miyuki Ishizaki; Osamu Hoshino

Publisher: John Wiley and Sons
Year: 2003
Tongue: English
Weight: 92 KB
Volume: 15
Category: Article
ISSN: 0899-0042
DOI: 10.1002/chir.10204

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✦ Synopsis

Abstract

Novel C~2~‐symmetrical chiral sulfides were synthesized from (R,R)‐tartaric acid and their utility in the asymmetric epoxidation of aldehydes with benzyl bromide was examined. Among the sulfides used, silyl ether‐type sulfides were found to be superior to diol‐ and benzyl ether‐type sulfides. Also, the presence of an aromatic group on the sulfide was proven to be an important factor for increasing enantioselectivity. Chirality 15:300–305, 2003. © 2003 Wiley‐Liss, Inc.

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