alpha-Hypervalent iodine functionalized phosphonium and arsonium ylides and their tandem reaction as umpolung reagents

Zhizhen Huang; Xiaochun Yu; Xian Huang

doi:10.1021/jo026077i

alpha-Hypervalent iodine functionalized phosphonium and arsonium ylides and their tandem reaction as umpolung reagents

J Org Chem. 2002 Nov 15;67(23):8261-4. doi: 10.1021/jo026077i.

Authors

Zhizhen Huang¹, Xiaochun Yu, Xian Huang

Affiliation

¹ Department of Chemistry, Zhejiang University, Xixi Campus, Hangzhou 310028, P. R. China.

PMID: 12423166
DOI: 10.1021/jo026077i

Abstract

alpha-Hypervalent iodine functionalized phosphonium and arsonium ylides 2 can be used as umpolung ylides to react with nucleophiles to give alpha-heteroatom substituted ylides 4 in good yields. The nucleophilic substitution-Wittig tandem reaction of 2 can occur smoothly to provide an efficient method for the synthesis of (Z)-alpha-halo-alpha,beta-unsaturated enoates or enones 6, stereoselectively.