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Synfacts 2009(11): 1281-1281  
DOI: 10.1055/s-0029-1218113
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Guanidinium Salt Catalyzed Imine Hydrophosphonylation

Contributor(s): Benjamin List, Lars Ratjen
X. Fu, W.-T. Loh, Y. Zhang, T. Chen, T. Ma, H. Liu, J. Wang, C.-H. Tan*
National University of Singapore, Singapore
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Publication History

Publication Date:
22 October 2009 (online)

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Significance

The authors report new chiral guanidinium salts such as 1 as catalysts for the phospha-Mannich reaction between N-tosyl ­imines and phosphine oxides or benzyl phosphinates, respectively. The catalysts were synthesized by simply mixing the corresponding diamine 2 and the pyrrolidinium salt 3 under basic conditions. The α-amino phosphine oxides and phosphinates were obtained in high yields, good dia­stereo- and high enantioselectivities.

Review: D. Leow, C.-H. Tan Chem. Asian J. 2008, 4, 488-507.