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Synfacts 2009(12): 1352-1352  
DOI: 10.1055/s-0029-1218321
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Catalytic Enantioselective Synthesis of Ring-Fused Tetrahydroquinolines

Contributor(s): Hisashi Yamamoto, Dmitry L. Usanov
S. Murarka, I. Deb, C. Zhang, D. Seidel*
Rutgers, The State University of New Jersey, Piscataway, USA
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Publication History

Publication Date:
20 November 2009 (online)

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Significance

The intramolecular hydride shift-ring closure sequence allows rapid molecular complexity generation. Unlike oxidative C-H activation protocols, this transformation does not involve ­redox processes. The authors report the first catalytic enantioselective protocol of this type providing access to tetrahydroquinolines. Under optimized conditions a number of variously substituted products were prepared in good to excellent yields (72-97%) and high enantioselectivities (up to 93% ee). Diastereomeric ratios ranged from 50:50 to 90:10.