The reduction of several p-substituted aromatic aldehydes by zinc in the presence of boron trifluoride and cyclic or open chain olefins, vinyl or allyl ethers or acetates, leads to the corresponding substituted arylcyclopropanes by way of carbene intermediates.
Facile Synthesis of Optically Active Tertiary Alcohol Building Blocks by Stereospecific C–H Insertion Reaction of Dichlorocarbene with Secondary Alcohol Derivatives
作者:Yukio Masaki、Hideki Arasaki、Motoo Shiro
DOI:10.1246/cl.2000.1180
日期:2000.10
Stereospecific C–H insertion of dichlorocarbene generated from a system CHCl3/50%NaOH/cetyltrimethylammonium chloride (as a PTC) proceeded at the carbinol carbon in the reaction of chiral secondary alcohol derivatives to provide α-dichloromethylated tertiary alcohol derivatives with complete retention of configuration.