Modulating steric effects in diastereoselective staudinger reaction : Synthesis of optically pure cis-β-lactams

Tetrahedron

Volumn 52, Issue 10, 1996, Pages 3741-3756

  Jayaraman, M ^a   Srirajan, V ^a   Deshmukh, A R A S ^a   Bhawal, B M ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAM DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030051583     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00048-8     Document Type: Article

References (24)

1. Staudinger, M. Liebigs. Ann. Chem. 1907, 356, 51.
2. For a review on a chiral control of the Staudinger reaction see: a) Cooper, R. D. G.; Daughery, B. W.; Boyd, D. B. Pure Appl. Chem. 1987, 59, 485.
3. b) Georg, G. I.; Ravikumar, V. T. In The Chemistry of β-lactams; G. I. Georg, Ed.; VCH. New York, 1993, p 295.
4. a) Hubschwerlen, C.; Schmid, G. Helv. Chim. Acta., 1983, 66, 2206.
5. b) Wagle, D. R.; Garai, C.; Chiang, J.; Monteleone, M. G.; Kurys, B. E.; Strohmeyer, T. W.; Hegde, V. R.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1988, 53, 4227.
6. c) Kawabata, T.; Kimura, Y.; Ito, Y.; Terashima, S.; Sasaki, A.; Sunagawa, M. Tetrahedron 1988, 44, 2149.
7. d) Bose, A. K.; Womelsdorf, J. F.; Krishnan, L.; Urbanczyk-Lipkowska, Z.; Shelly, D. C.; Manhas, M. S. Tetrahedron 1991, 47, 5379.
8. e) Palomo, C.; Cossio, F. P.; Cuevas, C.; Lecca, B.; Mielgo, A.; Roman, P.; Luque, A.; Martinez-Ripoll, M. J. Am. Chem. Soc. 1992, 114, 9360.
9. Jayaraman, M.; Deshmukh, A. R. A. S.; Bhawal, B. M. Synlett, 1992, 9, 749.
10. (a) Matsui, M.; Yoshioka, H.; Sakamoto, H.; Yamad, Y.; Kitahara, T. Agric. Biol. Chem. 1967, 31, 33.
11. (b) Mitra, R. B.; Kulkarni, G. H.; Muljiani, Z.; Khanna, P. N. Synth. Commun. 1988, 18, 1139.
12. (c) Deshmukh, A. R. A. S. Ph. D. Thesis, University of Poona, 1984. matrix presented
13. Wagle, D. R.; Garai, C.; Chiang, J.; Monteleone, M. G.; Kurys, B. E.; Strohmeyer, T. W.; Hegde, V. R.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1988, 53, 4227.
14. 2O (60:40), flow rate 2 mL/min.
15. (a) Ojima, I.; Chen, H. C. J. Chem. Soc. Chem. Commun, 1987, 625.
16. (b) Ojima, I.; Chen, H. C.; Qiu, X. Tetrahedron, 1988, 44, 5307.
17. (c) Alcaide, B.; Dominguez, G.; Escobar, G.; Parreno, V.; Plumet. J. Heterocycles, 1986, 24, 1579.
18. Omura, K.; Swern, D. Tetrahedron, 1978, 34, 1651.
19. b) Mancuso, A. J.; Swern, D. Synthesis, 1981, 165.
20. (a) Cocker, W.; Lauder, H. St. J. J. Chem. Soc., Perkin Trans. 1 1974, 194.
21. (b) Kropp, P. J.; Heckert, D. C.; Flault, T. J. Tetrahedron, 1968, 24, 1385.
22. Bachi, M. D.; Vaya, J. J. Org. Chem. 1979, 44, 4393.
23. Greenlee, M. L.; DiNinno, F. P.; Salzmann, T. N. Heterocycles, 1989, 28, 195.
24. Kronenthal, D. R.; Han, C. Y.; Taylor, M. K. J. Org. Chem. 1982, 47, 2765.