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J Org Chem. 2011 Jan 21;76(2):396-402. doi: 10.1021/jo101717m. Epub 2010 Dec 30.

Enantioselective organocatalytic Biginelli reaction: dependence of the catalyst on sterics, hydrogen bonding, and reinforced chirality.

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1
Department of Chemistry, Indian Institute of Technology, Kanpur 208016, India.

Abstract

From a systematic investigation involving the synthesis of a series of catalysts and screening studies, the organocatalyst 16, which is sterically hindered, contains a strong hydrogen-bonding site, and is endowed with reinforced chirality, is shown to promote the Biginelli cyclocondensation of aromatic as well as aliphatic aldehydes with ethyl acetoacetate and urea in a remarkably high enantioselectivity (ee ca. 94-99%).

PMID:
21192642
DOI:
10.1021/jo101717m

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