Synthesis and evaluation of a novel dirhodium tetraprolinate catalyst containing bridging prolinate ligands

Tetrahedron Letters

Volumn 38, Issue 24, 1997, Pages 4203-4206

  Davies, Huw M L ^a   Kong, Norman ^a  

^a UNIVERSITY AT BUFFALO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE DERIVATIVE; RHODIUM COMPLEX;

ARTICLE; CATALYST; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROMETRY; MASS SPECTROMETRY; METHODOLOGY; REACTION ANALYSIS;

EID: 0031006750     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00897-6     Document Type: Article

References (18)

1. (a) Davies, H. M. L.; Hutcheson, D. K. Tetrahedron Lett. 1993, 34, 7243.
2. (b) Davies, H. M. L.; Peng, Z. Q.; Houser, J. H. Tetrahedron Lett. 1994, 35, 8939.
3. Davies, H. M. L.; Bruzinski, P. R.; Lake, D. H.; Kong, N.; Fall, M. J. J. Am. Chem. Soc. 1996, 118, 6897.
4. Corey, E. J.; Gant, T. G. Tetrahedron Lett. 1994, 35, 5373.
5. (a) Davies, H. M. L.; Bruzinski, P. R.; Fall, M. J. Tetrahedron Lett. 1996, 37, 4133.
6. (b) Doyle, M. P.; Zhou, Q. -L.; Charnsangavej, C.; Longoria, M. A.; McKervey, M. A.; Garcia, C. F. Tetrahedron Lett. 1996, 37, 4129.
7. Doyle, M. P. Recl. Trav. Chim. Pays-Bas 1991, 110, 305. Singh, V. K.; DataGupta, A.; Sekar, G. Synthesis 1996, 137.
8. Doyle, M. P. Recl. Trav. Chim. Pays-Bas 1991, 110, 305. Singh, V. K.; DataGupta, A.; Sekar, G. Synthesis 1996, 137.
9. (a) Brunner, J.; Kluschanzoff, H.; Wutz, K. Bull. Soc. Chim. Belg. 1989, 98, 63.
10. (b) Ferris, L.; Haigh, D.; Moody, C. J. Tetrahedron Lett. 1996, 37, 107.
11. (a) Halterman, R. L.; Mei, X. Tetrahetron Lett. 1996, 37, 6291.
12. (b) Maxwell, J. L.; O'Malley, S.; Brown, K. C.; Kodadek, T. Organometallics 1992, 11, 645.
13. O'Malley, S.; Kodadek, T. Organometallics 1992, 11, 2299.
14. (a) Beck, A. K.; Blank, S.; Job, K.; Seebach, D.; Sommerfeld, T. Org. Syn. 1993, 72, 62.
15. (b) Seebach, D.; Boes, M.; Naef, R.; Schweizer, W. B. J. Am. Chem. Soc. 1983, 105, 5390.
16. 4 (M + H), 1651.3580, found (m + H) 1651.3603.
17. Modeling studies of 5c bound to dirhodium show that the up-down arrangement of the sulfonyl groups is 27 Kcal/mole more stable than the up-up arrangement.
18. R = 14 min (1R, 2R), 17 min (1S, 2S).