AlEt3-promoted eliminative ring-opening of β-hydroxy epoxides: highly stereoselective synthesis of terminal α-hydroxy olefins
摘要:
AlEt3-promoted eliminative ring-opening of beta-epoxy alcohols leading to alpha-hydroxy olefins is reported. This eliminative ring-opening reaction is shown to be highly stereoselective, thus providing an alternative asymmetric synthesis for a-hydroxy olefins. (C) 2003 Elsevier Ltd. All rights reserved.
The reactions of trialkylstannylmethyllithium with α,β-epoxyketones afforded mainly cyclopropanols, while α-chloro ketones afforded allyl alcohols and/or cyclopropanols, in varying amounts depending upon the molar ratio of the reagent to the substrate.