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Synfacts 2008(5): 0509-0509  
DOI: 10.1055/s-2008-1072636
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Allylic Alkylation with ‘Hard’ Amide Carbanions

Contributor(s): Hisashi Yamamoto, Joshua N. Payette
K. Zhang, Q. Peng, X.-L. Hou, Y.-D. Wu*
Shanghai Institute of Organic Chemistry and Hong Kong University of Science and Technology, P. R. of China
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Publikationsdatum:
23. April 2008 (online)

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Significance

Until the work of Trost and Schroeder (J. Am. Chem. Soc. 1999, 121, 6759), transition-metal-catalyzed asymmetric allylic alkylation (AAA) reactions were confined to the use of ‘soft’, stabilized carbanions. However, general methods to apply carboxylic acid carb­anions in AAA reactions remain undeveloped. As a large step forward, the authors report the use of acyclic amides as nucleophiles in the Pd-catalyzed AAA reaction with 1,1′-P,N ferrocene ligand L1. Alkylation of a variety of α-substituted aliphatic and aromatic amides proceeded in high yield with good to high levels of asymmetric induction.