Organic letters

Pyran annulation: asymmetric synthesis of 2, 6-disubstituted-4-methylene tetrahydropyrans

GE Keck, JA Covel, T Schiff, T Yu

Index: Keck, Gary E; Covel, Jonathan A; Schiff, Tobias; Yu, Tao Organic letters, 2002 , vol. 4, # 7 p. 1189 - 1192

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Citation Number: 79

Abstract

A reaction process for the asymmetric construction of a variety of cis or trans disubstituted pyrans is described. This sequences allows for the asymmetric convergent union of two aldehydes with silyl-stannane reagent 1 in a two-step process: catalytic asymmetric allylation of the first aldehyde using 1 with a BITIP catalyst, followed by reaction of the alcohol so obtained with a second aldehyde and TMSOTf.

~89%

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