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Synfacts 2011(1): 0050-0050  
DOI: 10.1055/s-0030-1259171
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Hydrophosphonylation of Ynones

Contributor(s): Mark Lautens, Jane Panteleev
D. Uraguchi, T. Ito, S. Nakamura, T. Ooi*
Nagoya University, Japan
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Publication History

Publication Date:
21 December 2010 (online)

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Significance

Hydrophosphonylation of carbonyl-containing compounds (Pudovik reaction) is a useful way of accessing chiral alkyl phosphonates, but addition to ketones is usually problematic (see Review below). The authors report a hydrophosphonylation of alkynoates utilizing the tetra­aminophosphonate catalyst 1. The authors initially reported an application of 1 to an asymmetric addition of phosphonates to aldehydes (J. Am. Chem. Soc. 2009, 131, 3836).

Review: P. Merino, E. Marqués-López, R. P. Herrera Adv. Synth. Catal. 2008, 350, 1195-1208.