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

Saha, Satyajit ; Narasimha Moorthy, Jarugu (2011) Enantioselective organocatalytic biginelli reaction: dependence of the catalyst on sterics, hydrogen bonding, and reinforced chirality Journal of Organic Chemistry, 76 (2). pp. 396-402. ISSN 0022-3263

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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo101717m

Related URL: http://dx.doi.org/10.1021/jo101717m

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%).

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:60754
Deposited On:10 Sep 2011 11:42
Last Modified:10 Sep 2011 11:42

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