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Synfacts 2008(11): 1180-1180  
DOI: 10.1055/s-0028-1083442
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Mannich Reaction of β-Keto Phosphonate with a Dinuclear Ni Complex

Contributor(s): Hisashi Yamamoto, Joshua N. Payette
Z. Chen, K. Yakura, S. Matsunaga*, M. Shibasaki*
The University of Tokyo, Japan
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Publication History

Publication Date:
23 October 2008 (online)

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Significance

In related work, Jørgensen has reported the first asymmetric direct Mannich-type reaction of β-keto phosphonates (A. Kjærsgaard, K. A. Jørgensen Org. Biomol. Chem. 2005, 3, 804). However, this process was limited to the use of N-Ts-imino esters. In the present study, the Shibasaki group has shown that a homodinuclear Ni2-Schiff base complex catalyzes the addition of β-keto phosphonates to N-Boc aryl imines. This system tolerates a range of electronically diverse aryl imines giving products in moderate to high ­diastereomeric ratios and excellent enantiomeric excesses.