Effect of conformational control of chiral oxazaborolidine by π-π stacking interaction of a pentafluorophenyl group toward asymmetric borane reduction期刊界 All Journals 搜尽天下杂志传播学术成果专业期刊搜索期刊信息化学术搜索

Effect of conformational control of chiral oxazaborolidine by π-π stacking interaction of a pentafluorophenyl group toward asymmetric borane reduction

Authors:	Toshinobu Korenaga

Affiliation:	Division of Chemistry and Biochemistry, Graduate School of Natural Science and Technology, Okayama University, Okayama 700-8530, Japan

Abstract:	A pentafluorophenyl group can act as a stereo-controlling group in oxazaborolidine-catalyzed asymmetric borane reduction through intramolecular π-π stacking interaction with a phenyl group. The intramolecular π-π interaction in oxazaborolidine bearing pentafluorophenyl group is confirmed by calculations and ¹H NMR study. The interaction affects the enantioselectivity of the asymmetric reduction of acetophenone while the extent is small.

Keywords:	Pentafluorophenyl group Oxazaborolidine π-π stacking Asymmetric borane reduction
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