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Asymmetric Carbon−Carbon Bond Formation γ to a Carbonyl Group: Phosphine-Catalyzed Addition of Nitromethane to Allenes

2009; American Chemical Society; Volume: 131; Issue: 40 Linguagem: Inglês

10.1021/ja9061823

1943-2984

Sean W. Smith, Gregory C. Fu,

Asymmetric Hydrogenation and Catalysis

A chiral phosphine catalyzes the addition of a carbon nucleophile to the γ position of an electron-poor allene (amide-, ester-, or phosphonate-substituted), in preference to isomerization to a 1,3-diene, in good ee and yield. This strategy provides an attractive method for the catalytic asymmetric γ functionalization of carbonyl (and related) compounds.