4.8 Article

Formal [4+1]- and [5+1]-Annulation by an SN2-Conjugate Addition Sequence: Stereoselective Synthesis of Highly Substituted Carbocycles

Journal

ORGANIC LETTERS
Volume 14, Issue 11, Pages 2826-2829

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol301044e

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Funding

  1. Nanyang Technological University
  2. Singapore Ministry of Education

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K2CO3-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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