Issue 3, 2017

Iridium-catalyzed asymmetric hydrogenation of racemic α-substituted lactones to chiral diols

Abstract

We report a protocol for the highly efficient iridium-catalyzed asymmetric hydrogenation of racemic α-substituted lactones via dynamic kinetic resolution. Using Ir-SpiroPAP (R)-1d as a catalyst, a wide range of chiral diols were prepared in a high yield (80–95%) with a high enantioselectivity (up to 95% ee) under mild reaction conditions. This protocol was used for enantioselective syntheses of (−)-preclamol and a chiral 2,5-disubstituted tetrahydropyran.

Graphical abstract: Iridium-catalyzed asymmetric hydrogenation of racemic α-substituted lactones to chiral diols

Supplementary files

Article information

Article type
Edge Article
Submitted
15 Oct 2016
Accepted
14 Nov 2016
First published
15 Nov 2016
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2017,8, 1811-1814

Iridium-catalyzed asymmetric hydrogenation of racemic α-substituted lactones to chiral diols

X. Yang, H. Yue, N. Yu, Y. Li, J. Xie and Q. Zhou, Chem. Sci., 2017, 8, 1811 DOI: 10.1039/C6SC04609F

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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