Addition of organozinc species to cyclic 1,3-diene monoepoxide

Song Xue; Yali Li; Kaizhen Han; Wen Yin; Meng Wang; Qingxiang Guo

doi:10.1021/ol017279o

Addition of organozinc species to cyclic 1,3-diene monoepoxide

Org Lett. 2002 Mar 21;4(6):905-7. doi: 10.1021/ol017279o.

Authors

Song Xue¹, Yali Li, Kaizhen Han, Wen Yin, Meng Wang, Qingxiang Guo

Affiliation

¹ Department of Chemistry, University of Science and Technology of China, Hefei, 230026, P R China. xuesong@ustc.edu.cn

PMID: 11893182
DOI: 10.1021/ol017279o

Abstract

[reaction: see text] The reaction of organozinc reagents (ZnEt(2), ZnPh(2)) with cyclic 1,3-diene monoepoxides in the presence of CF(3)COOH gave the cis-addition products. Lewis acids such as (CF(3)CO(2))(2)Zn and ZnCl(2) mediated the nucleophilic addition of ZnEt(2) to cyclooctadiene monoepoxide with high stereoselectivity.