Issue 8, 2011
From the journal:

Organic & Biomolecular Chemistry

Asymmetric syn-selective direct aldol reaction of protected hydroxyacetone catalyzed by primary amino acid derived bifunctional organocatalyst in the presence of water†

Akshay Kumar,a   Sarbjit Singh,a   Vikas Kumara  and  Swapandeep Singh Chimni*a  

* Corresponding authors

a Department of Chemistry, U.G.C. Centre of Advance Studies in Chemistry, Guru Nanak Dev University, Amritsar, India
E-mail: sschimni@yahoo.com, sschimni.chem@gndu.ac.in
Fax: +91-183-2258820
Tel: +91-183-2258809

Abstract

A new series of water compatible primary-tertiary diamine catalysts derived from natural primary amino acids bearing a hydrophobic side chain have been synthesized. These new primary-tertiary diamine-Brønsted acid conjugates bifunctional organocatalysts efficiently catalyzes the asymmetric direct syn selective cross-aldol reaction of different protected hydroxyacetone with various aldehydes in high yield (94%) and high enantioselectivity (up to 97% ee of syn) and dr of 91 : 9 (syn/anti) under mild reaction conditions.

Graphical abstract: Asymmetric syn-selective direct aldol reaction of protected hydroxyacetone catalyzed by primary amino acid derived bifunctional organocatalyst in the presence of water

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Article information

DOI
https://doi.org/10.1039/C0OB00898B
Article type
Paper
Submitted
18 Oct 2010
Accepted
10 Jan 2011
First published
11 Jan 2011

Org. Biomol. Chem., 2011,9, 2731-2742

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Asymmetric syn-selective direct aldol reaction of protected hydroxyacetone catalyzed by primary amino acid derived bifunctional organocatalyst in the presence of water

A. Kumar, S. Singh, V. Kumar and S. Singh Chimni, Org. Biomol. Chem., 2011, 9, 2731 DOI: 10.1039/C0OB00898B

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