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Synfacts 2009(8): 0867-0867  
DOI: 10.1055/s-0029-1217444
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Palladium-Catalyzed Kinetic Resolution of Nitrogen Nucleophiles

Contributor(s): Mark Lautens, Jane Panteleev
X. L. Hou*, B. H. Zheng
Shanghai Institute of Organic Chemistry, P. R. of China
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Publikationsdatum:
23. Juli 2009 (online)

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Significance

In this work, the authors report an original kinetic resolution of indoline nucleophiles in a palladium-catalyzed allylic substitution. The enantioselectivities of starting materials and products are moderate to good. While a variety of ­resolutions of racemic allyl substrates through transition-metal-catalyzed allylation exist (i.e. E. M. Carreira and co-workers J. Am. Chem. Soc. 2004, 126, 1628; K. Onitsuka et al. Organometallics 2005, 24, 6472), this is reported to be the first example of a resolution of nucleophiles.

Review: For a Review on kinetic resolution, see: J. M. Keith, J. F. Larrow, E. N. Jacobsen Adv. Synth. Catal. 2001, 343, 5-26.