Download PDF
Synfacts 2011(6): 0624-0624  
DOI: 10.1055/s-0030-1260388
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of 2,3-Disubstituted Indolines by Asymmetric Hydrogenation

Contributor(s): Mark Lautens, Stephen G. Newman
D.-S. Wang, J. Tang, Y.-G. Zhou*, M.-W. Chen, C.-B. Yu, Y. Duan, G.-F. Jiang*
Dalian Institute of Chemical Physics and Hunan University, Changsha, P. R. of China
Further Information

Publication History

Publication Date:
19 May 2011 (online)

    Permissions and Reprints

Significance

Asymmetric hydrogenation of ­heterocycles is a challenging transformation due to the need to destroy aromaticity. The authors have previously developed a method for activating unprotected indoles for hydrogenation (J. Am. Chem. Soc. 2010, 132, 8909). In the present report, they utilize 3-(α-hydroxyalkyl)indoles, which can be activated by dehydration, allowing for a highly enantioselective palladium-catalyzed ­hydrogenation to take place.