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Synfacts 2009(6): 0647-0647  
DOI: 10.1055/s-0029-1217199
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Chiral α-Branched Allylic Amines by Addition of Alkenyltrifluoroborates

Contributor(s): Hisashi Yamamoto, Joshua N. Payette
K. Brak, J. A. Ellman*
University of California, Berkeley, USA
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Publication History

Publication Date:
25 May 2009 (online)

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Significance

While rhodium(I)-catalyzed addition of arylboron reagents to imines is known prior to this study, related alkenylboron additions have not been reported. The authors disclose the rhodium(I)-catalyzed addition of alkenyltrifluoroborates to chiral aromatic and aliphatic N-tert-butanesulfinyl imines which proceeds in excellent yields and diastereoselectivities. Furthermore, the use of tri- and tetrasubstituted trifluoroborates is equally ­tolerated. In several cases, alkenylations with electron-deficient trifluoroborates afforded lower yields (22-66%).