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Trans-stereoselectivity in the reaction between homophthalic anhydride and imines.

Authors :
Vara Y
Bello T
Aldaba E
Arrieta A
Pizarro JL
Arriortua MI
Lopez X
Cossío FP
Source :
Organic letters [Org Lett] 2008 Nov 06; Vol. 10 (21), pp. 4759-62. Date of Electronic Publication: 2008 Sep 25.
Publication Year :
2008

Abstract

The reaction between homophthalic anhydride and imines in the presence of TiCl4 and diisopropyl ethyl amine is trans-selective. Under these conditions, the reaction using homochiral imines can be highly diastereoselective, thus allowing the synthesis of enantiopure 1,2,3,4-tetrahydro-1-oxoquinoline-4-carboxylic acids.

Details

Language :
English
ISSN :
1523-7052
Volume :
10
Issue :
21
Database :
MEDLINE
Journal :
Organic letters
Publication Type :
Academic Journal
Accession number :
18816130
Full Text :
https://doi.org/10.1021/ol801757r