prolinethioamides versus prolinamides in organocatalyzed aldol reactions—a comparative studyprolinethioamides和prolinamides organocatalyzed醇醛反应比较研究.pdfVIP

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prolinethioamides versus prolinamides in organocatalyzed aldol reactions—a comparative studyprolinethioamides和prolinamides organocatalyzed醇醛反应比较研究.pdf

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prolinethioamides versus prolinamides in organocatalyzed aldol reactions—a comparative studyprolinethioamides和prolinamides organocatalyzed醇醛反应比较研究

Symmetry 2011, 3, 265-282; doi:10.3390/sym3020265 OPEN ACCESS symmetry ISSN 2073-8994 /journal/symmetry Review Prolinethioamides versus Prolinamides in Organocatalyzed Aldol Reactions—A Comparative Study Dorota Gryko *, MikołajChromińskiand Dominika J. Pielacińska Institute of Organic Chemistry PAS, Kasprzaka 44/52, 01-224 Warsaw, Poland; E-Mails: mikolaj.chrominski@ (M.C.); dominika-lodz@o2.pl (D.J.P.) * Author to whom correspondence should be addressed; E-Mail: dorota.gryko@.pl; Tel.: +48 22 343 21 19; Fax: +48 22 632 66 81. Received: 7 February 2011; in revised form: 23 May 2011 / Accepted: 24 May 2011/ Published: 1 June 2011 Abstract: Various organocatalysts have been developed for the aldol reaction but particular attention has been paid to prolinamide derivatives. They are easy to prepare and their catalytic activity can be readily tuned through structural modification. In this review, the comparison of catalytic activities between prolinethioamides and their respective amides in direct asymmetric aldol reactions is presented. Keywords: organocatalysis; prolinethioamides; prolinamides; aldol reaction; enamine-iminium catalysis 1. Introduction Organocatalysis can be defined as the acceleration of a chemical reaction using a substoichiometric amount of an organic compound. Its application in enantioselective catalysis has recently emerged as a major concept in asymmetric synthesis, although organic molecules have been used as catalysts since the beginning of chemistry [1–8]. Until 2000, only a limited number of preparativ