Journal
TETRAHEDRON-ASYMMETRY
Volume 13, Issue 1, Pages 29-36Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0957-4166(02)00043-5
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N-(Phenylthiomethyl)oxazolidinones derived from camphor can be lithiated and added to aldehydes in good yields and stereoselectivities. The adducts are crystalline, which simplifies isolation of the major diastereomer from the product mixture. Hydrolysis affords enantiopure alpha-hydroxy aldehydes, which can be oxidized to alpha-hydroxy acids in good yields. The steric course of the reaction is analyzed in detail and a mechanistic model is presented. (C) 2002 Elsevier Science Ltd. All rights reserved.
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