Domino carbopalladation-carbonylation: generating quaternary stereocenters while controlling beta-hydride elimination.

Org Lett

Organic Chemistry, KTH Chemical Science and Engineering, Royal Institute of Technology, SE-10044 Stockholm, Sweden.

Published: September 2010

A domino carbopalladation-carbonylation sequence for substrates possessing beta-hydrogens is explored. This allows for the construction of complex architectures with vicinal stereocenters in a concise and rapid fashion via the stereocontrolled formation of two carbon-carbon bonds. An integral aspect of this domino reaction is the ability to control beta-hydride elimination of the organopalladium intermediate and instead form the carbonylation product.

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http://dx.doi.org/10.1021/ol1009703DOI Listing

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A domino carbopalladation-carbonylation sequence for substrates possessing beta-hydrogens is explored. This allows for the construction of complex architectures with vicinal stereocenters in a concise and rapid fashion via the stereocontrolled formation of two carbon-carbon bonds. An integral aspect of this domino reaction is the ability to control beta-hydride elimination of the organopalladium intermediate and instead form the carbonylation product.

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