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Synfacts 2009(10): 1118-1118  
DOI: 10.1055/s-0029-1217841
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Allylic Amination and Kinetic Resolution of Allylic Carbonates

Contributor(s): Mark Lautens, Chit Tsui
D. C. Vrieze*, G. S. Hoge, P. Z. Hoerter, J. T. Van Haitsma, B. M. Samas
Pfizer Global Research and Development, Ann Arbor, USA
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Publikationsdatum:
22. September 2009 (online)

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Significance

The current work represents a ­novel method for the kinetic resolution of unsymmetrical acyclic allylic carbonates and the concurrent synthesis of enantioenriched secondary amines using a commercially available chiral catalyst (S,S,R,R)-Tangphos-Rh. The corresponding carbonate 2 and amine 3 products can be obtained with excellent yields and enantioselectivities. The reaction is also scalable (10 mmol) with the requirement of only 0.5 mol% of the catalyst.