Probing electronic effects in the asymmetric heck reaction with the BIPI ligands

Organic Letters

Volumn 5, Issue 4, 2003, Pages 595-598

  Busacca, Carl A ^a   Grossbach, Danja ^a,b   So, Regina C ^a   O'Brien, Erin M ^a   Spinelli, Earl M ^a  

^a BOEHRINGER INGELHEIM PHARMACEUTICALS INC   (United States)

^b BAYER PHARMA AG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

IMIDAZOLINE DERIVATIVE; LIGAND; PHOSPHINE; IMIDAZOLE DERIVATIVE; PHOSPHINE DERIVATIVE;

ARTICLE; ASYMMETRIC CATALYSIS; CHIRALITY; DENSITY; ELECTRONICS; ENANTIOSELECTIVITY; HECK REACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; STEREOCHEMISTRY; CATALYSIS; CHEMISTRY; ELECTRON; STEREOISOMERISM;

CATALYSIS; ELECTRONS; IMIDAZOLES; LIGANDS; PHOSPHINES; STEREOISOMERISM;

EID: 0038345075     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0340179     Document Type: Article

References (14)

1. Busacca, Carl A. U.S. Patent 6,316,620, 2001. Boehringer-Ingelheim Phosphinoimidazolines. For a recent application of the BIPI ligands to asymmetric hydrogenation, see: Menges, F.; Neuburger, M.; Pfaltz, A. Org. Lett. 2002, 4, 4713.
2. Busacca, Carl A. U.S. Patent 6,316,620, 2001. Boehringer-Ingelheim Phosphinoimidazolines. For a recent application of the BIPI ligands to asymmetric hydrogenation, see: Menges, F.; Neuburger, M.; Pfaltz, A. Org. Lett. 2002, 4, 4713.
3. For a review, see: Helmchen, G.; Pfaltz, A. Acc. Chem. Res. 2000, 33(6), 336-345.
4. Full experimental details for all ligands are found in Supporting Information.
5. (a) Kraatz, H.-B.; Pletsch, A. Tetrahedron: Asymmetry 2000, 11, 1617.
6. (b) Imamoto, T.; Oshiki, T.; Onozawa, T.; Kusumoto, T.; Sato, K. J. Am. Chem. Soc. 1990, 112, 5244.
7. (a) Ohsaka, T.; Che, Y.; Tokuda, K. Bull. Chem. Soc. Jpn. 1998, 71, 651.
8. (b) James, H. J.; Broman, R. F. Anal. Chim. Acta 1969, 48, 411.
9. (a) Loiseleur, O.; Hayashi, M.; Schmees, N.; Pfaltz, A. Synthesis 1997, 1338.
10. (b) Ozawa, F.; Hayashi, T. J. Organomet. Chem. 1992, 428, 267.
11. (c) Ozawa, F.; Kobatake, Y.; Hayashi, T. Tetrahedron Lett. 1993, 34, 2505.
12. (a) Ashimori, A.; Bachand, B.; Overman, L. E.; Poon, D. J. J. Am. Chem. Soc. 1998, 120, 6477.
13. (b) Ashimori, A.; Bachand, B.; Calter, M. A.; Govek, S. P.; Overman, L. E.; Pooh, D. J. J. Am. Chem. Soc. 1998, 120, 6488.
14. Full details of the effect of bases on turnover will be reported shortly in a full paper.