Asymmetric Hydrogenation of Alkynyl Ketones with the η6-Arene/TsDPEN–Ruthenium (II) Catalyst

N Arai, H Satoh, N Utsumi, K Murata, K Tsutsumi…

Index: Arai, Noriyoshi; Satoh, Hironori; Utsumi, Noriyuki; Murata, Kunihiko; Tsutsumi, Kunihiko; Ohkuma, Takeshi Organic Letters, 2013 , vol. 15, # 12 p. 3030 - 3033

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Citation Number: 24

Abstract

Enantioselective hydrogenation of alkynyl ketones catalyzed by Ru (OTf)(TsDPEN)(η6-p- cymene)(TsDPEN= N-(p-toluenesulfonyl)-1, 2-diphenylethylenediamine) affords the propargylic alcohols in up to 97% ee. The alkynyl moieties are left intact in most cases. The reaction can be conducted with a substrate-to-catalyst molar ratio as high as 5000 under 10 atm of H2. The mode of enantioselection is elucidated with the transition state models ...