Journal of the American Chemical Society

Asymmetric syntheses based on 1, 3-oxathianes. 2. Synthesis of chiral tertiary. alpha.-hydroxy aldehydes,. alpha.-hydroxy acids, glycols [R1R2C (OH) CH2OH], and …

JE Lynch, EL Eliel

Index: Lynch, Joseph E.; Eliel, Ernest L. Journal of the American Chemical Society, 1984 , vol. 106, # 10 p. 2943 - 2948

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Citation Number: 146

Abstract

Abstract: A chiral 1, 3-oxathiane (5) prepared from (+)-pulegone in three steps is converted to diastereomerically pure equatorial 2-acyl derivatives by lithiation, condensation with aldehydes, and Me, SO oxidation. Reaction of the resulting ketones with Grignard reagents at-78 OC again proceeds highly stereoselectively (diastereomer excess generally above 90%) according to Cram's rule (cyclic model). The resulting tertiary carbinols when ...