Enantioselective construction of quaternary carbon centers by catalytic [2 + 2 + 2] cycloaddition of 1,6-enynes and alkynes

Takanori Shibata; Yoshikazu Arai; Yu-Ki Tahara

doi:10.1021/ol051876j

Enantioselective construction of quaternary carbon centers by catalytic [2 + 2 + 2] cycloaddition of 1,6-enynes and alkynes

Org Lett. 2005 Oct 27;7(22):4955-7. doi: 10.1021/ol051876j.

Authors

Takanori Shibata¹, Yoshikazu Arai, Yu-Ki Tahara

Affiliation

¹ Department of Chemistry, School of Science and Engineering, Waseda University, Shinjuku, Tokyo, Japan. tshibata@waseda.jp

PMID: 16235931
DOI: 10.1021/ol051876j

Abstract

[reaction: see text] The enantioselective [2 + 2 + 2] cycloaddition of 1,6-enynes and alkynes using chiral rhodium catalysts gave cycloadducts containing quaternary carbon stereocenters. Both symmetrical and unsymmetrical alkynes and acetylene could be used as coupling partners, and the corresponding bicyclic cyclohexa-1,3-dienes were obtained in good to excellent ee.