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Synlett 2010(6): 881-884  
DOI: 10.1055/s-0029-1219543
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Chiral Bifunctional (Thio)Urea N-Heterocyclic Carbenes

Jonathan P. Brand, José Ignacio Osuna Siles, Jérôme Waser*
Laboratory of Catalysis and Organic Synthesis, Ecole Polytechnique Fédérale de Lausanne, EPFL SB ISIC LCSO, BCH 4306, 1015 Lausanne, Switzerland
Fax: +41(21)6939700; e-Mail: jerome.waser@epfl.ch;
Further Information

Publication History

Received 14 December 2009
Publication Date:
23 February 2010 (online)

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Abstract

The rapid and modular synthesis of the first bifunctional N-heterocyclic carbenes bearing a (thio)urea moiety as H-bond donor group was reported. Different analogues could be accessed in seven steps from cheap (S)-pyroglutamic acid in good overall yields (14-30%). The synthesized carbenes were active catalysts in the benzoin reaction.

Key words

umpolung - asymmetric catalysis - carbenes - homogeneous catalysis - chiral pool

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