Direct asymmetric three-component organocatalytic anti-selective Mannich reactions in a purely aqueous system

The direct three-component Mannich reactions of O-benzyl hydroxyacetone with p-anisidine and aromatic or aliphatic aldehydes in the presence of an L-threonine-derived catalyst afforded anti-1,2-amino alcohols in good-to-excellent yields and with enantioselectivities of up to 97%. This study is the f...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2007-01, Vol.5 (7), p.1018-1020
Main Authors: Cheng, Lili, Wu, Xiaoyu, Lu, Yixin
Format: Article
Language:English
Subjects:
Aldehydes - chemistry
Amino Alcohols - chemical synthesis
Amino Alcohols - chemistry
Aniline Compounds - chemistry
Benzene Derivatives - chemistry
Catalysis
Molecular Structure
Stereoisomerism
Threonine - chemistry
Water - chemistry
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Summary:The direct three-component Mannich reactions of O-benzyl hydroxyacetone with p-anisidine and aromatic or aliphatic aldehydes in the presence of an L-threonine-derived catalyst afforded anti-1,2-amino alcohols in good-to-excellent yields and with enantioselectivities of up to 97%. This study is the first demonstration that direct three-component Mannich reactions can be promoted by a primary amino acid in water.
ISSN:1477-0520
1477-0539
DOI:10.1039/b701579h