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Synfacts 2011(9): 0993-0993  
DOI: 10.1055/s-0030-1261039
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Nickel-Catalyzed Enantioselective α-Chlorination

Contributor(s): Mark Lautens, Stephen G. Newman
Y. Hamashima, T. Nagi, R. Shimizu, T. Tsuchimoto, M. Sodeoka*
RIKEN Advanced Science Institute, Saitama, Meiji University, Kawasaki and Saitama University, Japan
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Publikationsdatum:
19. August 2011 (online)

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Significance

Chiral alkyl chlorides are useful substrates in synthesis due to their stereospecific reactivity with a range of nucleophiles. One of the most important processes to prepare optically active chlorinated compounds is through enantio­selective α-halogenation reactions (see Review below). Building on previous work in fluorination reactions (Sodeoka and co-workers Angew. Chem. Int. Ed. 2007, 46, 5435), the authors present an asymmetric α-chlorination of oxazoli­dinone derivatives of arylacetic acid using a Ni/BINAP catalyst.

Review: S. France, A. Weatherwax, T. Lectka Eur. J. Org. Chem. 2005 , 475-479.