Tetrahedron Letters

Enone structure as a probe to Lewis acid carbonyl binding in copper-catalysed asymmetric conjugate addition

C Börner, WA König, S Woodward

Index: Boerner, Christoph; Koenig, Wilfried A.; Woodward, Simon Tetrahedron Letters, 2001 ,  vol. 42,  # 2  p. 327 - 329

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Citation Number: 19

Abstract

Systematic changes in the substitution pattern of linear enones (R1COCH CHR2) helps identify the reactive conformation (s-trans versus s-cis) of the enone in copper-catalysed asymmetric 1, 4-ZnEt2 addition. Pointers to the binding mode of the Lewis Acid (syn or anti to the 'ene'function) are also gathered. Enantioselectivities of up to 79% have been realised in these reactions.