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Synfacts 2008(7): 0730-0730  
DOI: 10.1055/s-2008-1078461
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Proline Derivatives and α-Aryl Aminoesters via N-H Insertion

Contributor(s): Mark Lautens, Frédéric Ménard
Q.-H. Deng, H.-W. Xu, A. W.-H. Yuen, Z.-J. Xu*, C.-M. Che*
Shanghai Institute of Organic Chemistry and The University of Hong Kong, P. R. of China
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Publikationsdatum:
20. Juni 2008 (online)

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Significance

The method uses a commercially available Ru(II) complex and shows an impressive scope. Intermolecular cases allow the use of primary and secondary amines, as well as sulfon­amides, amides and carbamates. In intramolecular cases, a wide range of all-cis-substituted pyrrolidines can be obtained with high stereocontrol. Notably, the method was shown to be insensitive to air, moisture, and solvent. Indeed, the intermolecular reaction worked equally well (94-98%) in any non-protic solvent.