Transition metal-free access to 3,4-dihydro-1,2-oxaphosphinine-2-oxides from phosphonochloridates and chalcones through tandem Michael addition and nucleophilic substitution?

Chemical Communications Pub Date: 2019-10-08 DOI: 10.1039/C9CC06352H

Abstract

A novel and transition metal-free synthesis of 3,4-dihydro-1,2-oxaphosphinine 2-oxides was developed. LiHMDS-mediated tandem Michael addition and nucleophilic substitution of readily available phosphonochloridates and chalcones afforded a variety of valuable 3,4-dihydro-1,2-oxaphosphinine 2-oxides bearing diverse functionalities in excellent yields and satisfactory to good diastereoselectivity (up to 99% yield and up to 99?:?1 dr).

Graphical abstract: Transition metal-free access to 3,4-dihydro-1,2-oxaphosphinine-2-oxides from phosphonochloridates and chalcones through tandem Michael addition and nucleophilic substitution
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