Phosphonium salt induced stereoselective allylic rearrangement during chlorination of α-hydroxyallylphosphinates

α-Hydroxyallylphosphinates were stereoselectively converted to γ-chloro allylphosphinates when treated with Ph3P and CCl4, via substitution of hydroxyl and migration of double bond. The reaction was promoted by phosphonium cation that acted as Lewis acid.

Saved in:
Bibliographic Details
Published in:Tetrahedron letters 2014-10, Vol.55 (42), p.5742-5744
Main Authors: Ji, Si-Yu, Sun, Yong-Ming, Zhang, He, Hou, Qing-Gao, Zhao, Chang-Qiu
Format: Article
Language:English
Subjects:
Chlorination
Lewis acid
Phosphonium
Rearrangement
γ-Chloro allylphosphinate
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:α-Hydroxyallylphosphinates were stereoselectively converted to γ-chloro allylphosphinates when treated with Ph3P and CCl4, via substitution of hydroxyl and migration of double bond. The reaction was promoted by phosphonium cation that acted as Lewis acid.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2014.08.118