- Preparation of α-haloacrylate derivatives via dimethyl sulfoxide-mediated selective dehydrohalogenation
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(Chemical Equation Presented) Dimethyl sulfoxide causes α/β-dihalopropanoate derivatives to undergo efficient, selective dehydrohalogenation to form α-haloacrylate analogues. A variety of α-halo Michael acceptors were prepared in dimethyl sulfoxide under mild, base-free conditions, including the preparation of α-bromoacrolein and α-chloro- and bromoacrylonitriles. Synthesis of these molecules has been reported in the literature to be difficult. Among all the existing dehydrohalogenation procedures, this protocol is the most facile, practical, and environmentally benign process.
- Li, Wei,Li, Jianchang,Wan, Zhao-Kui,Wu, Junjun,Massefski, Walter
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p. 4607 - 4610
(2008/03/13)
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- Enantioselective Preparation of Polyfunctional Secondary Allylic Alcohols Using Functionalized Dialkylzincs Prepared by a Copper(I) Catalyzed Iodine-Zinc Exchange Reaction.
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Catalytic amounts of Cu(I) salts considerably facilitate the iodine-zinc exchange reaction leading to polyfunctional dialkylzincs.The catalytic asymmetric addition of these zinc reagents to a wide range of α,β-unsaturated aldehydes provides polyfunctional allylic alcohols with a high enantioselectivity.
- Rozema, Michael J.,Eisenberg, Christina,Luetjens, Henning,Ostwald, Roswitha,Belyk, Kevin,Knochel, Paul
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p. 3115 - 3118
(2007/10/02)
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