Metal Catalyzed Alkene Functionalization: An Approach Toward Stereospecific Cross-Coupling
Stereospecific cross-coupling of chiral alkyl metal intermediates is a recognized challenge in modern organic synthesis. Here an alternative strategy is presented in which a chiral alkyl metal is generated as a catalytic intermediate by boryl-metalation of an alkene.1-5 This method represents an attractive approach in chemical synthesis because two new bonds and two new stereocenters are generated in a single operation. In addition, due to the synthetic versatility of the carbon-boron bond, a variety of structures can be readily prepared, thus representing a general approach toward carbofunctionalization of alkenes. The scope, mechanistic details, and application to complex molecule synthesis will be discussed.
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