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Synfacts 2009(12): 1372-1372  
DOI: 10.1055/s-0029-1218241
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Copper Bisoxazoline Catalyzed Enantioselective S-H Insertion

Contributor(s): Mark Lautens, Stephen G. Newman
Y.-Z. Zhang, S.-F. Zhu, Y. Cai, H.-X. Mao, Q.-L. Zhou*
Nankai University, Tianjin, P. R. of China
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Publication History

Publication Date:
20 November 2009 (online)

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Significance

The authors report an enantioselective synthesis of α-mercaptoesters by insertion of S-H bonds into copper carbenoids generated from α-diazoesters. The use of their spiro bisoxazoline (spirobox) ligands is the key to attaining high yields and selectivity. The free thiol could be obtained by using trityl thiol for S-H insertion followed by mild deprotection without loss of enan­tiomeric excess (one example). This work is an ­extension of previous methodologies on insertion into N-H and O-H bonds using a similar catalytic system (J. Am. Chem. Soc. 2007, 129, 5834; J. Am. Chem. Soc. 2007, 129, 12616).