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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 38, 2008 - Issue 23
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Original Articles

Organocatalytic, Asymmetric, One-Pot, Three-Component Mannich Reaction of Hydroxyacetone

, , , &
Pages 4198-4206 | Received 27 Feb 2008, Published online: 31 Oct 2008
 

Abstract

The direct three-component asymmetric Mannich reactions of hydroxyacetone with anilines and aromatic aldehydes in the presence of (2S,5S)-5-(methoxycarbonyl)pyrrolidine-2-carboxylic acid afforded syn-1,2-amino alcohols in good-to-excellent yields (55∼91%) and up to 98% ee.

ACKNOWLEDGMENT

We thank the National Natural Science Foundation of China (20402004) and the Science Foundation of Shanghai Municipality (06ZR14028) for financial support.

Notes

a Isolated yield after silica-gel column chromatography.

b Determined by HPLC analysis.

c Ee values of syn-isomer, determined by HPLC using chiralpak AD-H column.

d 4 Å Molecular sieves were added.

e The reaction was carried out at 10 °C.

f Performed imine was used.

a Isolated yield after column chromatography.

b Determined by HPLC analysis.

c Enantiomeric excess of syn-product was determined by HPLC using Chiralcel OD-H or Chiralpak AD-H column.

a Isolated yield after silica-gel column chromatography.

b Determined by HPLC analysis.

c Ee values of syn-isomer, determined by HPLC using Chiralpak AD-H column.

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