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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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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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Publication details

The article was received on 15 Aug 2019, accepted on 08 Oct 2019 and first published on 08 Oct 2019


Article type: Communication
DOI: 10.1039/C9CC06352H
Chem. Commun., 2019, Advance Article

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

    Z. Fu, S. Sun, A. Yang, F. Sun and J. Xu, Chem. Commun., 2019, Advance Article , DOI: 10.1039/C9CC06352H

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