Synthesis of P-chirogenic diarylphosphinoacetic acids and their proline derivatives for palladium-catalysed allylic alkylation reactions

Tetrahedron Letters

Volumn 46, Issue 47, 2005, Pages 8145-8148

  Lam, Hubert ^a,d   Horton, Peter N ^b   Hursthouse, Michael B ^b   Aldous, David J ^c   King, Kuok Hii ^a  

^a KING'S COLLEGE LONDON   (United Kingdom)

^b UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

^c SANOFI   (France)

^d FLORIDA STATE UNIVERSITY   (United States)

Author keywords

Allylic alkylation; Chirogenic phosphine; Palladium; PNP ligands

Indexed keywords

ACETIC ACID DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; PALLADIUM; PHOSPHINIC ACID DERIVATIVE; PROLINE; PROLINE DERIVATIVE;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; ENANTIOMER;

EID: 27144447062     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.09.136     Document Type: Article

References (20)

1. P. Barbaro, C. Bianchini, G. Giambastiani, and A. Togni Chem. Commun. 2002 2672 2673
2. S. Deerenberg, P.C.J. Kamer, and P.W.N.M. van Leuween Organometallics 19 2000 2065 2072
3. W. Tang, W. Wang, and X. Zhang Angew Chem., Int. Ed. 42 2003 943 946
4. D. Carmichael, H. Doucet, and J.M. Brown Chem. Commun. 1999 261 262
5. K. Burgess, M.J. Ohlmeyer, and K.H. Whitmire Organometallics 11 1992 3588 3600
6. X. Cheng, and K.K. Hii Tetrahedron: Asymmetry 14 2003 2045 2052
7. H. Lam, X. Cheng, J.W. Steed, D.J. Aldous, and K.K. Hii Tetrahedron Lett. 43 2002 5875 5877
8. H. Danjo, M. Higuchi, M. Yada, and T. Imamoto Tetrahedron Lett. 45 2004 603 606
9. A. Ohashi, K. Kikuchi, M. Yasutake, and T. Imamoto Eur. J. Org. Chem. 15 2002 2535 2546
10. A. Ohashi, and T. Imamoto Tetrahedron Lett. 42 2001 1099 1101
11. A. Ohashi, and T. Imamoto Org. Lett. 3 2001 373 375
12. Diarylphosphinoacetic acid-borane complex has been prepared by kinetic resolution of the corresponding menthyl esters T. Imamoto, T. Oshiki, T. Onozawa, T. Kusumoto, and K. Sato J. Am. Chem. Soc. 112 1990 5244 5252
13. S. Jugé, M. Stephan, J.A. Laffitte, and J.P. Genêt Tetrahedron Lett. 31 1990 6357 6360
14. A).
15. H. Inoue, Y. Nagaoka, and K. Tomioka J. Org. Chem. 67 2002 5864 5867
16. S.L. You, Y.M. Luo, W.P. Deng, X.L. Hou, and L.X. Dai J. Organomet. Chem. 637 2001 845 849
17. G. Knühl, P. Sennhenn, and G. Helmchen J. Chem. Soc., Chem. Commun. 1995 1845 1846
18. A. Yamazaki, T. Morimoto, and K. Achiwa Tetrahedron: Asymmetry 4 1993 2287 2290
19. Y. Okada, T. Minami, Y. Umezu, S. Nishikawa, R. Mori, and Y. Nakayama Tetrahedron: Asymmetry 2 1991 667 682
20. 4, filtered, evaporated, and filtered through a short plug of silica to afford a viscous oil. Enantiomeric excess was determined by chiral HPLC using a Chiralpak AD column.