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Synfacts 2005(3): 0324-0324  
DOI: 10.1055/s-2005-916141
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Kinetic Resolution of Dihydroxybiaryls via Asymmetric Transfer Vinylation

Contributor(s): Mark Lautens, Andrew Martins
H. Aoyama, M. Tokunaga*, J. Kiyosu, T. Iwasawa, Y. Obora, Y. Tsuji*
Hokkaido University, and SORST, CREST & JST, Sapporo, Japan
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Publikationsdatum:
22. November 2005 (online)

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Significance

Optically active BINOL and its derivatives are typically obtained via optical resolution or chiral pool methods. This communication represents the first reported use of asymmetric transfer vinylation in the kinetic resolution of BINOL and dihydroxybiaryl derivatives. Using a chiral diamine ligand in the presence of Pd(OAc)2 and an alcohol, a single atropisomer can be devinylated with moderate to high selectivity (krel = 6.1-41.2) under the optimized reaction conditions.