Chiral Brønsted Acid-Catalyzed Direct Asymmetric Mannich Reaction

A chiral Brønsted acid-catalyzed direct asymmetric Mannich reaction has been described. Various phosphoric acids, prepared from BINOL and H8-BINOL derivatives, have been evaluated for catalyzing the direct Mannich reaction. In the presence of a truly catalytic amount of the phosphoric acid, anti-sel...

Full description

Saved in:
Bibliographic Details
Published in:Journal of the American Chemical Society 2007-04, Vol.129 (13), p.3790-3791
Main Authors: Guo, Qi-Xiang, Liu, Hua, Guo, Chang, Luo, Shi-Wei, Gu, Yi, Gong, Liu-Zhu
Format: Article
Language:English
Subjects:
Acids - chemistry
Catalysis
Ketones - chemistry
Mannich Bases - chemistry
Molecular Structure
Stereoisomerism
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:A chiral Brønsted acid-catalyzed direct asymmetric Mannich reaction has been described. Various phosphoric acids, prepared from BINOL and H8-BINOL derivatives, have been evaluated for catalyzing the direct Mannich reaction. In the presence of a truly catalytic amount of the phosphoric acid, anti-selective Mannich reactions of cyclic ketones with a wide scope of aldimines were obtained in high yields with excellent enantioselectivities (up to 98% ee) and high diastereomeric ratios (up to 98/2 dr). A one-pot Mannich reaction using aromatic ketones as donors proceeded smoothly to give β-amino carbonyls with fairly good enantioselectivities.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja068236b