Organic & Biomolecular Chemistry 2011-04-21

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

Akshay Kumar, Sarbjit Singh, Vikas Kumar, Swapandeep Singh Chimni

Index: Org. Biomol. Chem. 9(8) , 2731-42, (2011)

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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.