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P(NMe2)3-Mediated Reductive (1+4) Annulation Reaction of α-Keto Esters with Nitroalkenes: A Facile Synthesis of Polysubstituted Isoxazoline N-Oxides.

Authors :
Yiyi Liu
Kanghui Lu
Tao Wan
Jiaqiang Wei
Junjie Wu
Shangkun Gong
Song Xu
Zhengjie He
Source :
ChemistrySelect; 5/7/2021, Vol. 6 Issue 17, p4400-4403, 4p
Publication Year :
2021

Abstract

A P(NMe<subscript>2</subscript>)<subscript>3</subscript>-mediated reductive (1+4) annulation reaction of αketo esters with substituted nitroalkenes has been developed, providing a feasible protocol to construct polysubstituted isoxazoline N-oxides in moderate to excellent yields from readily available starting materials. This reaction originates from the characteristic reactivity of in situ generated KukhtinRamirez adducts and presumably proceeds through a tandem Michael addition-intramolecular S<subscript>N</subscript>2 sequence. To further expand the utility of this annulation reaction, isoxazolines have been efficiently prepared from corresponding annulation products upon treatment with trimethyl phosphite. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
23656549
Volume :
6
Issue :
17
Database :
Complementary Index
Journal :
ChemistrySelect
Publication Type :
Academic Journal
Accession number :
150780744
Full Text :
https://doi.org/10.1002/slct.202004503