Chiral 2, 2-disubstituted cyclohexanones; annulation via Claisen rearrangement products

TJ Grattan, JS Whitehurst

Index: Grattan, T. J.; Whitehurst, J. S. Journal of the Chemical Society, Chemical Communications, 1988 ,  # 1  p. 43 - 44

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Citation Number: 4

Abstract

The methyl enol ether of 2-methylcyclohexanone (S)-but-3-en-2-01 to give respectively, the (R)- and ... We considered it likely that a compound of type (1) would undergo the Claisen rearrangement1 stereoselectively, because its two possible chair-like transition states2 differ in that the R' group is quasi-equatorial in one and quasi-axial in the other. The expected products are (2) (major) and (3) (minor), respectively (see Scheme 1). For a synthetic project based on this idea ...