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Synfacts 2010(1): 0109-0109  
DOI: 10.1055/s-0029-1218486
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Steglich Rearrangement Using Isothiourea Catalysts

Contributor(s): Benjamin List, Olga Lifchits
C. Joannesse, C. P. Johnston, C. Concellón, C. Simal, D. Philp, A. D. Smith*
University of St. Andrews, UK
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Publication History

Publication Date:
21 December 2009 (online)

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Significance

Smith and colleagues report isothiourea catalysts 3 and 4 in the enantioselective carboxy group transfer of oxazolyl carbonates 1 (the Steglich rearrangement). The origin of stereo­control by these nucleophilic catalysts was studied by computational means. C4-α-Alkyl-branched oxazolyl carbonates were demonstrated to undergo the rearrangement with both catalysts (product 2a), expanding the scope of the transformation to this challenging class of substrates.