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A Switch of Facial Selectivities Using α-Heteroatom-Substituted Aldehydes in the Vinylogous Mukaiyama Aldol Reaction

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journal contribution
posted on 2009-03-19, 00:00 authored by Mariko Shinoyama, Shin-ichi Shirokawa, Atsuo Nakazaki, Susumu Kobayashi
The vinylogous Mukaiyama aldol reaction (VMAR) of chiral nonracemic ketene silyl N,O-acetal with various aldehydes is demonstrated. VMAR with α-heteroatom-unsubstituted aldehydes proceeded with a high degree of anti-selectivity. In sharp contrast, moderate to high syn-selectivity was observed when α-heteroatom-substituted aldehydes were used.

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