Asymmetric Henry Reaction Catalyzed by Novel Chiral Bioxazolines from Tartaric Acid

Kaluvu Balaraman; Ravichandran Vasanthan; Venkitasamy Kesavan

doi:10.1055/s-0031-1289811

Synthesis, Inhaltsverzeichnis

Synthesis 2012; 44(15): 2455-2462
DOI: 10.1055/s-0031-1289811

paper

Asymmetric Henry Reaction Catalyzed by Novel Chiral Bioxazolines from Tartaric Acid

Kaluvu Balaraman

Chemical Biology Laboratory, Department of Biotechnology, Bhupat and Jyothi Mehta School of Biosciences Building, Indian Institute of Technology Madras, Chennai 600036, India, Fax: +91(44)22574102 eMail: vkesavan@iitm.ac.in

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Ravichandran Vasanthan

Chemical Biology Laboratory, Department of Biotechnology, Bhupat and Jyothi Mehta School of Biosciences Building, Indian Institute of Technology Madras, Chennai 600036, India, Fax: +91(44)22574102 eMail: vkesavan@iitm.ac.in

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Venkitasamy Kesavan*

Chemical Biology Laboratory, Department of Biotechnology, Bhupat and Jyothi Mehta School of Biosciences Building, Indian Institute of Technology Madras, Chennai 600036, India, Fax: +91(44)22574102 eMail: vkesavan@iitm.ac.in

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Abstract

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Abstract

Novel C ₂-symmetric chiral bioxazolines were synthesized in good yields by the fusion of optically active acids with a tartaric acid derivative. Complexes of these products with copper(II) acetate monohydrate were found to be excellent catalysts for the Henry reaction, giving various nitro alcohols in very good yields and up to 84% enantiomeric excess. Although only five-membered chelation is possible with these ligands, they give better enantioselectivities than other bioxazoline ligands that undergo similar coordination.

Key words

asymmetric catalysis - aldol reactions - heterocyclic compounds - nitro compounds - alcohols

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