Diastereoselective chelation-controlled additions to β-silyloxy aldehydes.

Org Lett

P. Roy and Diana T. Vagelos Laboratories, University of Pennsylvania, Department of Chemistry, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, USA.

Published: July 2012

A general diastereoselective method for the addition of dialkylzincs and (E)-di- and (E)-trisubstituted vinylzinc reagents to β-silyloxy aldehydes is presented. This method employs alkyl zinc triflate and nonaflate Lewis acids and affords chelation-controlled products (6:1 to > 20:1 dr).

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3401491PMC
http://dx.doi.org/10.1021/ol301354wDOI Listing

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