Enantioselective deprotonation of protected 4-hydroxycyclohexanones
M Majewski, J MacKinnon
Index: Majewski, Marek; Mackinnon, John Canadian Journal of Chemistry, 1994 , vol. 72, # 7 p. 1699 - 1704
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Citation Number: 30
Abstract
A series of derivatives of 4-hydroxycyclohexanone (1 ag) with the hydroxy group protected as a silyl ether (1 a, b), ether (1 d, g), an acetal (1 c), or an ester (1 e, f) were deprotonated with chiral, optically pure, lithium amides 3-9. The resulting non-racemic enolates were trapped as enol acetates. The enantioselectivity of deprotonation was up to 74% ee.
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