Formal [4 + 1]- and [5 + 1]-annulation by an S(N)2-conjugate addition sequence: stereoselective synthesis of highly substituted carbocycles.

Org Lett

Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore.

Published: June 2012

K(2)CO(3)-mediated reactions of 6-bromo-2-hexenoates and 7-bromo-2-heptenoate with active methylene compounds deliver highly substituted cyclopentane and cyclohexane derivatives, respectively via a sequence of S(N)2-conjugate addition reactions (formal [4 + 1]- and [5 + 1]-annulation) in a diastereoselective manner.

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Source
http://dx.doi.org/10.1021/ol301044eDOI Listing

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