A general approach to high-yielding asymmetric synthesis of chiral 3-alkyl-4-nitromethylchromans via cascade Barbas-Michael and acetalization reactions

A general approach to the high-yielding asymmetric synthesis of chiral 3-alkyl-4-nitromethylchromans as drug intermediates was achieved through cascade Barbas-Michael and acetalization (BMA) reactions on 2-(2-nitrovinyl)phenols with aldehydes in the presence of a catalytic amount of (R)-DPPOTMS and...

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Veröffentlicht in:	Organic & biomolecular chemistry 2011-04, Vol.9 (8), p.2715-2721
Hauptverfasser:	Ramachary, Dhevalapally B, Prasad, M Shiva, Madhavachary, R
Format:	Artikel
Sprache:	eng
Schlagworte:	Acetals - chemistry Alkylation Catalysis Chromones - chemical synthesis Methylation Molecular Structure Nitro Compounds - chemistry Stereoisomerism
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creator	Ramachary, Dhevalapally B Prasad, M Shiva Madhavachary, R
description	A general approach to the high-yielding asymmetric synthesis of chiral 3-alkyl-4-nitromethylchromans as drug intermediates was achieved through cascade Barbas-Michael and acetalization (BMA) reactions on 2-(2-nitrovinyl)phenols with aldehydes in the presence of a catalytic amount of (R)-DPPOTMS and PhCO(2)H. Herein, we have also demonstrated the application of chiral BMA products in the synthesis of functionalized chromanes and chromenes in very good yields with high optical purity, which are very useful compounds in medicinal chemistry.
doi_str_mv	10.1039/c0ob00861c
format	Article
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source	MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection
subjects	Acetals - chemistry Alkylation Catalysis Chromones - chemical synthesis Methylation Molecular Structure Nitro Compounds - chemistry Stereoisomerism
title	A general approach to high-yielding asymmetric synthesis of chiral 3-alkyl-4-nitromethylchromans via cascade Barbas-Michael and acetalization reactions
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