Design of an Axially Chiral Dicarboxylic Acid and Its Application in Syntheses of Optically Active β-Amino Acids and β-Amino Phosphonic Acid Derivatives

Abstract

An axially chiral dicarboxylic acid was developed as a new chiral Brønsted acid catalyst. With this novel catalyst in hand, N-Boc-protected β-amino acids or β-amino phosphonic acid derivatives could be obtained in high yields and enantioselectivities by asymmetric Mannich-type reaction of N-Boc imines and diazo compounds.

amino acids - asymmetric catalysis - carboxylic acids - diazo compounds - Mannich-type reaction

References

For recent reviews, see:

1a Doyle AG. Jacobsen EN. Chem. Rev.  2007,  107:  5713 

1b Akiyama T. Chem. Rev.  2007,  107:  5744 

2 Momiyama N. Yamamoto H. J. Am. Chem. Soc.  2005,  127:  1080 

3 Ooi T. Uematsu Y. Maruoka K. J. Org. Chem.  2003,  68:  4576 

4 Seki M. Yamada S. Kuroda T. Imashiro R. Shimizu T. Synthesis  2000,  1677 

5 Barder TE. Walker SD. Martinelli JR. Buchwald SL. J. Am. Chem. Soc.  2005,  127:  4685 

6 Hashimoto T. Maruoka K. J. Am. Chem. Soc.  2007,  129:  10054 ; and supporting information

7 Uraguchi D. Sorimachi K. Terada M. J. Am. Chem. Soc.  2005,  127:  9360