The Journal of organic chemistry

Synthesis of optically pure arylsilylcarbinols and their use as chiral auxiliaries in oxacarbenium ion reactions

JR Huckins, SD Rychnovsky

Index: Huckins, John R.; Rychnovsky, Scott D. Journal of Organic Chemistry, 2003 , vol. 68, # 26 p. 10135 - 10145

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Citation Number: 35

Abstract

A family of arylsilylcarbinols was synthesized and investigated as chiral auxiliaries for oxacarbenium ion reactions. The optically pure arylsilylcarbinols were prepared using Noyori's transfer hydrogenation catalyst 11. The transfer hydrogenation shows very good enantioselectivities and turnover efficiency for the aryl silyl ketones and is the method of choice for preparing these optically pure alcohols. The diastereoselective addition of ...

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