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Synfacts 2010(5): 0560-0560  
DOI: 10.1055/s-0029-1219637
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Reverse Regioselectivity in Amino-halogenation of Electron-Deficient Olefins

Contributor(s): Hisashi Yamamoto, Kimberly Griffin
S.-J. Zhi, H. Sun, G. Zhang, G. Li*, Y. Pan*
Nanjing University and Huaiyin Normal University, P. R. of China; Texas Tech University, Lubbock, USA
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Publikationsdatum:
22. April 2010 (online)

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Significance

A manganese catalyst system is employed in the aminohalogenation of β-methyl-β-nitrostyrenes. Interestingly, the regioselectivity of the reaction is the opposite of comparable aminohalogenation processes, with the chlorine moiety on the α-carbon of the nitroalkane. The method is a new approach to generating halogenated quaternary stereocenters.