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Enantioselective Biginelli Reaction

Posted by naturalproductman on June 30, 2009

Hee-Yoon Lee at KAIST has recently published in the European Journal of Organic Chemistry on a proline ester salt catalyzed asymmetric Biginelli reaction, which involves the coupling of an aryl aldehyde, urea, and a beta-ketoester to form a 3,4-dihydropyrimidin-2(1H)-one
(DHPM).  They used a t-butoxy proline ester (20 mol%) for optimal enantioselectivity (71:29).

biginelli reaction

European Journal of Organic Chemistry paper

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One Response to “Enantioselective Biginelli Reaction”

  1. Edinburgher said

    Wow awesome pic,

    So hard to get one of those multicomponent reactions to work selectively. The fact that it works with something as proline is really interesting.

    Thanks for the pic and the good work

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