4.8 Article

Stereoselective 1,6-Conjugate Addition/Annulation of para-Quinone Methides with Vinyl Epoxides/Cyclopropanes

Journal

ACS CATALYSIS
Volume 6, Issue 10, Pages 6408-6412

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acscatal.6b01845

Keywords

palladium catalysis; vinyl epoxide; vinyl cyclopropane; para-quinone methide; [3+2] cycloaddition

Funding

  1. Singapore National Research Foundation [R-143-000-477-281]
  2. Ministry of Education of Singapore [R-143-000-613-112]
  3. National University of Singapore [R-143-000-605-112]

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Here, we present an unprecedented formal [3 + 2] cycloaddition of para-quinone methides with vinyl epoxides/cyclopropanes to deliver a wide range of spiro[4.5]decanes in high efficiency and stereoselectivity. The commercial availability of the catalysts and reagents, together with the convenient procedure, makes it an attractive method in asymmetric synthesis.

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