Stereoselective Synthesis of<i>syn</i>-Configured α-Allenols by Rhodium-Catalyzed Reaction of Alkynyl Oxiranes with Arylboronic Acids
作者:Tomoya Miura、Masahiko Shimada、Paula de Mendoza、Carl Deutsch、Norbert Krause、Masahiro Murakami
DOI:10.1021/jo900987w
日期:2009.8.21
A rhodium-catalyzedreaction of alkynyloxiranes with arylboronicacids affords syn-configured α-allenols with high diastereoselectivity. The reaction is initiated by addition of an arylrhodium(I) species onto the alkyne moiety of the alkynyloxirane. The resulting alkenylrhodium(I) intermediate undergoes β-oxygen elimination to open the oxirane ring in a syn-selective fashion. Protonolysis of the