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Enantioselective NiH/Pmrox‐Catalyzed 1,2‐Reduction of α,β‐Unsaturated Ketones
Author(s) -
Chen Fenglin,
Zhang Yao,
Yu Lei,
Zhu Shaolin
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201610990
Subject(s) - enantioselective synthesis , catalysis , allylic rearrangement , yield (engineering) , chemistry , combinatorial chemistry , organic chemistry , materials science , metallurgy
The enantioselective 1,2‐reduction of α,β‐unsaturated ketones was achieved using a NiH catalyst in the presence of pinacolborane. This mild process represents a general method to access a wide variety of structurally diverse α‐chiral allylic alcohols in excellent yields and enantioselectivity, as well as very high levels of ambidoselectivity for 1,2‐ over 1,4‐reduction. Furthermore, for reactions on a 10 mmol scale, catalyst loadings as low as 0.5 mol % could be employed to deliver product without any detrimental effect on the yield, enantio‐, or ambidoselectivity.