Enantioselective NiH/Pmrox‐Catalyzed 1, 2‐Reduction of α, β‐Unsaturated Ketones. (16th January 2017)

• Record Type: Journal Article
• Authors: Chen, Fenglin; Zhang, Yao; Yu, Lei; Zhu, Shaolin
• Is Part Of: Angewandte Chemie. Volume 129:Number 8(2017)
• Page Start: 2054
• Page End: 2057
• Publication Date: 2017-01-16
• Subjects: α, β-ungesättigte Ketone -- 1, 2-Reduktionen -- Asymmetrische Katalyse -- Nickel -- Synthesemethoden; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201610990
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: 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.