Author(s):
Pinho e Melo, Teresa M. V. D. 
; Santos, Catarina I. A. ; Rocha Gonsalves, António M. dA. ; Paixão, José A. ; Beja, Ana M.
Date: 2004
Persistent ID: http://hdl.handle.net/10316/5137
Origin: Estudo Geral - Universidade de Coimbra
Subject(s): Diastereoselectivity; Thiazolo[2,3-a]isoindoles; 3-Methylene-2,5-oxazolo[2,3-a]isoindoles; [1.3]Thiazolo[3,2-c][1,3]benzoxazines
Description
The thermolysis of (3R,9bS)-5-oxo-2,3,5,9b-tetrahydrothiazolo[2,3-a]isoindole-3-carboxylic acids in Ac2O led to novel 3-methylene-2,5-dioxo-3H,9bH-oxazolo[2,3-a]isoindoles and chiral (9bS)-5-oxo-2,3,5,9b-tetrahydrothiazolo[2,3-a]isoindoles were obtained on FVP. Starting from -cysteine methyl ester (3R,10bR)-5-oxo-2,3-dihydro-10bH-[1.3]thiazolo[3,2-c][1,3]benzoxazines were obtained as single stereoisomers. The thermolysis of (3R,10bR)-5-oxo-2,3-dihydro-10bH-[1.3]thiazolo[3,2-c][1,3]benzoxazine-3-carboxylic acid in Ac2O gave 5-acetyl-2-phenyl-2,3-dihydrothiazole. The structures of methyl (3R,9bS)-5-oxo-2,3,5,9b-tetrahydrothiazolo[2,3-a]isoindole-3-carboxylate 1a and methyl (2R,4R)-N-chlorocarbonyl-2-(2-hydroxyphenyl)thiazolidine-4-carboxylate 9 were determined by X-ray crystallography. http://www.sciencedirect.com/science/article/B6THR-4C40YF0-8/1/7705fb68c2f9e77d90918a00a3d71e74
