Tetrahedron

Stereo-and enantioselective routes to functionalised cyclohexenes via heterodiene cycloadditions of 6-oxocyclohexene-1-carbaldehydes with ketene acetals

R Hayes, KD Li, P Leeming, TW Wallace, RC Williams

Index: Hayes, Roy; Li, Ke-Dong; Leeming, Peter; Wallace, Timothy W.; Williams, Richard C. Tetrahedron, 1999 , vol. 55, # 44 p. 12907 - 12928

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Citation Number: 10

Abstract

Various substituted cyclohexenes related to α-cyclocitral have been prepared using the heterodiene cycloadditions of 2-formyl-4, 4-dimethyl-2-cyclohexen-1-one 4 with ketene acetals as the pivotal step. The key intermediates are accessible in homochiral form via an auxiliary-based sequence in which a C2-symmetric ketene acetal derived from 1, 2-bis (2- methylphenyl) ethane-1, 2-diol 2a serves as the 2π component. The diol 2a can be ...