Issue 6, 2012

Copper(i)-catalyzed intramolecular [2 + 2] cycloaddition of 1,6-enyne-derived ketenimine: an efficient construction of strained and bridged 7-substituted-3-heterobicyclo[3.1.1]heptan-6-one

Abstract

The transformation of 1,6-enynes into bridged bicyclic systems was accomplished for the first time by a copper(I)-catalyzed tandem cycloaddition reaction. The reaction provides a straightforward approach for the synthesis of structurally diverse, strained and bridged bicycles in good yields with moderate to excellent diastereoselectivities.

Graphical abstract: Copper(i)-catalyzed intramolecular [2 + 2] cycloaddition of 1,6-enyne-derived ketenimine: an efficient construction of strained and bridged 7-substituted-3-heterobicyclo[3.1.1]heptan-6-one

Supplementary files

Article information

Article type
Edge Article
Submitted
26 Jan 2012
Accepted
09 Mar 2012
First published
12 Mar 2012

Chem. Sci., 2012,3, 1975-1979

Copper(I)-catalyzed intramolecular [2 + 2] cycloaddition of 1,6-enyne-derived ketenimine: an efficient construction of strained and bridged 7-substituted-3-heterobicyclo[3.1.1]heptan-6-one

B. Li, B. Yang, S. Wang, Y. Zhang, X. Cao and Y. Tu, Chem. Sci., 2012, 3, 1975 DOI: 10.1039/C2SC20109G

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