Stereoselective Synthesis of Thiochromenes via Intramolecular Tandem Thio-Michael Addition of in Situ Generated α,β-Unsaturated Aldehydes

An efficient and highly stereoselective strategy for the synthesis of 2,3-substituted thiochromenes having a complex and easily transformable group at the stereogenic center has been developed via a tandem thio-Michael addition reaction of an in situ generated α,β-unsaturated aldehyde sugar derivati...

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Bibliographic Details
Published in:Journal of organic chemistry 2014-04, Vol.79 (7), p.3111-3118
Main Authors: Kinfe, Henok Hadgu, Mebrahtu, Fanuel Mesfin, Makolo, Felix Loka, Moshapo, Paseka Thendo, Manana, Mandlenkosi Maxwell
Format: Article
Language:English
Subjects:
Aldehydes - chemical synthesis
Aldehydes - chemistry
Benzopyrans - chemical synthesis
Benzopyrans - chemistry
Carbohydrates - chemical synthesis
Carbohydrates - chemistry
Catalysis
Cyclization
Molecular Structure
Stereoisomerism
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Summary:An efficient and highly stereoselective strategy for the synthesis of 2,3-substituted thiochromenes having a complex and easily transformable group at the stereogenic center has been developed via a tandem thio-Michael addition reaction of an in situ generated α,β-unsaturated aldehyde sugar derivative. The protocol is superior to reported protocols in that the carbohydrate-derived substituent at the stereogenic center of the thiochromene is versatile and is amenable for further transformation.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo5002164