View PDF Version
 
DOI: 10.1039/A704353H (Paper) Reference Section for: J. Chem. Res. (S), 1997, 348-349

Asymmetric Synthesis. Part 2.† Enantioselective Conjugate Addition of Grignard Reagents to the Cinnamamide and Crotonamide deriving from (R)-(–)-N-(2-Fluorobenzyl)-2-aminobutanol. Determination of Diastereoisomeric Excess by 19F NMR Spectroscopy

(Note: The full text of this document is currently only available in the PDF Version )

Eric Brown, Christelle Deroye, François Huet, Christelle Le Grumelec and Joë Touet

Abstract

Conjugate addition of various Grignard reagents to the N-(2-fluorobenzyl)cinnamamide (R)-(+)-5 and crotonamide (R)-(+)-7 afforded the corresponding adducts 8a–e and 9a–f in good yields and in high diastereoisomeric excesses, as evidenced by 19F NMR; acidic hydrolysis of these adducts gave the corresponding β-substituted alkanoic acids (R)-10a–e and 11a–f, respectively.

References

  1. (a) J. Touet, S. Baudouin and E. Brown, J. Chem. Res. (S), 1996, 224 Search PubMed; (b) M. Shimano and A. I. Meyers, J. Org. Chem., 1995, 60, 7445 Search PubMed; (c) O. Melnyk, E. Stephan, G. Pourcelot and P. Cresson, Tetrahedron, 1992, 48, 841 Search PubMed; (d) E. Nicolas, K. C. Russel and V. J. Hruby, J. Org. Chem., 1993, 58, 766 Search PubMed.
  2. E. Brown, C. Chevalier, F. Huet, C. Le Grumelec, A. Lézé and J. Touet, Tetrahedron: Asymmetry, 1994, 5, 1191 Search PubMed.