Issue 10, 2015

A Ce(OTf)3/PyBox catalyzed enantioselective Hosomi–Sakurai reaction of aldehydes with allyltrimethylsilane

Abstract

An efficient enantioselective Hosomi–Sakurai reaction catalyzed by a chiral Ce(OTf)3/PyBox complex has been explored. In the presence of 20 mol% of a chiral catalytic complex prepared in situ from Ce(OTf)3 and 2,6-bis[(S)-4-isopropyloxazolin-2-yl]pyridine {(S)-i-Pr-PyBox} or tetraphenyl substituted (S)-i-PrPyBox, the enantioselective allylation of aldehydes with allyltrimethylsilane proceeded smoothly at room temperature and provided the homoallylic alcohols in good yield (up to 95%) and excellent enantioselectivities (up to 99%).

Graphical abstract: A Ce(OTf)3/PyBox catalyzed enantioselective Hosomi–Sakurai reaction of aldehydes with allyltrimethylsilane

Supplementary files

Article information

Article type
Letter
Submitted
13 Jun 2015
Accepted
22 Jul 2015
First published
23 Jul 2015

New J. Chem., 2015,39, 7734-7737

A Ce(OTf)3/PyBox catalyzed enantioselective Hosomi–Sakurai reaction of aldehydes with allyltrimethylsilane

S. Zhao, X. Zhang, Y. Zhang, H. Yang, Y. Huang, K. Zhang and T. Du, New J. Chem., 2015, 39, 7734 DOI: 10.1039/C5NJ01488C

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