Concepedia

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

Mariko Shinoyama, Shin‐ichi Shirokawa, Atsuo Nakazaki, Susumu Kobayashi

Organic Letters · 2009 · 50 citations · 17 references

DOI

Concepts

Abstract

The vinylogous Mukaiyama aldol reaction (VMAR) of chiral nonracemic ketene silyl N,O-acetal with various aldehydes is demonstrated. VMAR with alpha-heteroatom-unsubstituted aldehydes proceeded with a high degree of anti-selectivity. In sharp contrast, moderate to high syn-selectivity was observed when alpha-heteroatom-substituted aldehydes were used.

References

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