Use of asymmetric propargyl dicobalt hexacarbonyl complexes in organic synthesis: Access to enantiomerically pure α-hydroxy acid derivatives

Tetrahedron Letters

Volumn 39, Issue 52, 1998, Pages 9773-9776

  Betancort, Juan M ^a   Rodríguez, Carmen Ma ^a   Martín, Víctor S ^a  

^a UNIVERSIDAD DE LA LAGUNA   (Spain)

Author keywords

Asymmetric synthesis; Nicholas reaction

Indexed keywords

2 HYDROXYACID DERIVATIVE; CARBONYL DERIVATIVE; PROPARGYL DICOBALT HEXACARBONYL COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BINDING; CHIRALITY; ENANTIOMER; ORGANIC CHEMISTRY; REACTION ANALYSIS; STEREOISOMERISM; STRUCTURE ANALYSIS;

EID: 0032564615     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02170-4     Document Type: Article

References (26)

1. 1. (a) Caffyn, A. J. M.; Nicholas, K. M. In "Comprehensive Organometallic Chemistry-II". Hegedus, L. S., Ed. Pergamon: Oxford, 1995, Volume 12, Chapter 7.1, p. 685.
2. (b) Nicholas, K. M. Acc. Chem. Res. 1987, 20, 207.
3. 2. Krafft, M. E.; Cheung, Y. Y.; Wright, C.; Cali, R. J. Org. Chem. 1996, 61, 3912, and references cited therein.
4. 3. Schore, N. E. In "Comprehensive Organometallic Chemistry-II". Hegedus, L. S., Ed., Pergamon: Oxford, 1995, Volume 12, Chapter 7.2, p. 703.
5. 4. Schreiber, S. L.; Klimas, M. T.; Sammakia, T. J. Am. Chem. Soc. 1987, 109, 5749.
6. 5. Muehldorf, A. V.; Guzman-Perez, A.; Kluge, A. E. Tetrahedron Lett. 1994, 35, 8755
7. 6. Melikan, G. G.; Bright, S.; Monroe, T.; Handcastle, K. I. Ciurash, J. Angew. Chem. Int. Ed. Engl. 1998, 37, 161.
8. 7. (a) Bradley, D. H.; Khan, M. A.; Nicholas, K. M. Organometallics 1989, 8, 554.
9. (b) Ibid, ibid 1992, 11, 2598.
10. 8. Caffyn, A. J. M.; Nicholas, K. M. J. Am. Chem. Soc. 1993, 115, 6438.
11. 9. (a) Palazón, J. M.; Martín, V. S. Tetrahedron Lett. 1995, 36, 3549.
12. (b) Isobe, M.; Yenjai, C.; Tanaka, S. Synlett, 1994, 916.
13. (c) Tanaka, S.; Isobe, M. Tetrahedron Lett. 1994, 35, 7801.
14. (d) Ibid Tetrahedron 1994, 50, 5633.
15. (e) Tanaka, S.; Tsokiyama, T.; Isobe, M. Tetrahedron Lett. 1993, 34, 5757.
16. 10. (a) Jacobi, P. A.; Guo, J.; Zheng, W. Tetrahedron Lett. 1995, 36, 1197.
17. (b) Jacobi, P. A.; Zheng, W. ibid 1993, 34, 2581.
18. (c) Jacobi, P. A.; Rajeswan, S. ibid 1992, 33, 6231.
19. 11. Schreiber, S. L.; Sammakia, T.; Crowe, W. E. J. Am. Chem. Soc. 1986, 108, 3128.
20. 12. (a) Carlsen, P. H. J.; Katsuki, Y.; Martín, V. S., Sharpless, K. B. J. Org. Chem. 1981, 46, 3936.
21. (b) Núñez, M. T.; Martín, V. S. ibid 1990, 55, 1928.
22. (c) Martín, V. S.; Palazón, J. M.; Rodríguez, C. M. In "Encyclopedia of Reagent for Organic Synthesis". Paquette, L. A. Ed. Wiley: New York, 1995 Vol 6, p. 4415.
23. 13. In order to determine the absolute configuration, 17 was obtained by the following alternative synthetic sequence (see Martín, V. S.; Núñez, M. T.; Tonn, C. E. Tetrahedron Lett. 1988, 29, 2701): (formula presented)
24. 14. (a) Berger, D.; Overman, L. E. J. Am. Chem. Soc. 1997, 119, 2446.
25. (b) Melikyan, G. G.; Mineif, O.; Vostrowsky, O.; Bestmann, H. J. Synthesis 1991, 633.
26. (c) Saksena, A.K.; Green, M. J.; Mangiaracina, P.; Wong, J. K.; Kreutner, Gulbenkian, A.R. Tetrahedron Lett. 1985, 26, 6423.