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

✍ Scribed by Christoph Börner; Wilfried A König; Simon Woodward

• Publisher: Elsevier Science
• Year: 2001
• Tongue: French
• Weight: 65 KB
• Volume: 42
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)01940-7

✦ Synopsis

Systematic changes in the substitution pattern of linear enones (R 1 COCH CHR 2 ) helps identify the reactive conformation (s-trans versus s-cis) of the enone in copper-catalysed asymmetric 1,4-ZnEt 2 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.