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Synfacts 2007(2): 0164-0164  
DOI: 10.1055/s-2006-958969
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Selective Catalytic Bromoazidation of α,β-Unsaturated Carboxylic Acids

Contributor(s): Mark Lautens, Yann Béthuel
S. Hajra*, M. Bhowmick, D. Sinha
Indian Institute of Technology, Kharagpur, India
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Publication History

Publication Date:
23 January 2007 (online)

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Significance

Over the last few years, the authors were particularly interested in metal-catalyzed asymmetric halohydrinations of chiral α,β-unsaturated carboxylic acids (Tetrahedron Lett. 2005, 46, 3073-3077; Tetrahedron 2005, 61, 2279-2286; Tetrahedron: Asymmetry 2006, 17, 210-222). In the present paper, they extend the scope of the reactions possible on such substrates by developing a new efficient bromoazidation leading to chiral anti-α-bromo-β-azido carboxylic acids.