Oxazolidine-2-thiones and Thiazolidine-2-thiones as Nucleophiles in Intermolecular Michael Additions

Conjugate addition of thiazolidinethiones and oxazolidinethiones to N-crotonylthiazolidinethiones and -oxazolidinethiones was observed in the presence of excess triethylamine in dichloromethane. The addition takes place by the nitrogen of the heterocycle with high diastereoselectivity. It was observ...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2012-07, Vol.14 (13), p.3514-3517
Main Authors: Munive, Laura, Rivas, Veronica M, Ortiz, Aurelio, Olivo, Horacio F
Format: Article
Language:English
Subjects:
Molecular Structure
Thiones - chemical synthesis
Thiones - chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Conjugate addition of thiazolidinethiones and oxazolidinethiones to N-crotonylthiazolidinethiones and -oxazolidinethiones was observed in the presence of excess triethylamine in dichloromethane. The addition takes place by the nitrogen of the heterocycle with high diastereoselectivity. It was observed that the stereoselective addition occurs on the anti-s-cis conformation of the N-enoyl sulfur-containing heterocycle.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol301489y