Synfacts 2007(5): 0507-0507  
DOI: 10.1055/s-2007-968444
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed Regio- and Stereoselective Aminochlorinations

Contributor(s): Mark Lautens, Praew Thansandote
J.-L. Han, S.-J. Zhi, L.-Y. Wang, Y. Pan*, G. Li*
Nanjing University, P. R. of China and Texas Tech University, Lubbock, USA
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24. April 2007 (online)


A new method of obtaining vicinal haloamino nitriles is described using convenient catalytic conditions. Using CuI and molecular sieves, good yields and good regio- and stereo­selectivities are seen for aminochlorinations of tri- and tetrasubstituted cyano olefins. A moderate scope is shown with electron-withdrawing, electron-donating, and electron-neutral groups on the olefin to provide vicinal haloamino nitriles in good yields and stereoselectivities. Interestingly, opposite regiochemistries were seen for the α-substituted cinnamonitrile substrates compared to the β-substituted ones. For the latter substrates, the products of their aminochlorinations can be easily converted into desirable β-amino acids.