A stereoselective contrasteric conversion of epoxides to cis-oxazolidin-2-ones

Journal of the American Chemical Society

Volumn 110, Issue 23, 1988, Pages 7933-7935

  Trost, Barry M ^a   Sudhakar, Anantha R ^b  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

^b STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 OXAZOLIDINONE DERIVATIVE;

DRUG STRUCTURE; DRUG SYNTHESIS; METHODOLOGY; NONHUMAN; PRELIMINARY COMMUNICATION;

EID: 0023686086     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00231a085     Document Type: Article

References (10)

1. For alternative approaches, see: Shibata, I.; Baba, A.; Iwasaki, H.; Matsuda, H. J. Org. Chem. 1986, 51, 2177. Fujiwara, M.; Baba, A.; Tomohisa, Y.; Matsuda, H. Chem. Lett. 1986, 1963. Mereyala, H. B.; Frei, B. Helv. Chim. Acta 1986, 69, 415. Julina, R.; Herzig, T.; Bernet, B.; Vasella, A. Helv. Chim. Acta. 1986, 69, 368. Baba, A.; Fujiwara, M.; Matsuda, H. Tetrahedron Lett. 1986, 27, 77. Faroogi, J. A.; Ahmad, M. Chem. Ind. (London) 1985, 598. Baba, A.; Shibata, I.; Masuda, K.; Matsuda, H. Synthesis 1985, 1144 and references therein.
2. For a review, see: Dyen, M. E.; Swern, D.; Chem. Rev. 1967, 67, 197. Also, see: Roush, W. R.; Adam, M. A. J. Org. Chem. 1985, 50, 3752.
3. For reactions of chlorosulfonyl isocyanate, see: Lorincz, T.; Erden, I.; Nader, R.; deMeijere, A.; Synth. Commun. 1986, 16, 123. Murthy, K. S. K.; Dhar, D. N. Synth. Commun. 1984, 14, 7, 687.
4. For a novel synthesis of oxazolidin-2-ones from alkenes, see: Hu, N. X.; Aso, Y.; Otsubo, T.; Ogura, F. Chem. Commun. 1987, 1447.
5. Rosenberger, M.; Neukom, C.; Aig, E. R. J. Am. Chem. Soc. 1983, 105, 3656. Yoshimoto, M.; Ishida, N.; Kishida, Y. Chem. Pharm. Bull. 1971, 19, 863.
6. Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765.
7. Trost, B. M.; Sudhakar, A. R. J. Am. Chem. Soc. 1987, 109, 3792. Also, see: Hayashi, T.; Yamamoto, A.; Ito, Y. Tetrahedron Lett. 1988, 29, 99.
8. CAN = ceric ammonium nitrate. Kronenthal, D. R.; Han, C. Y.; Taylor, M. K. J. Org. Chem. 1982, 47, 2765.
9. Maehr, H.; Smallheer, J. J. Am. Chem. Soc. 1985, 107, 2943. Bradley, W.; Robinson, R. J. Am. Chem. Soc. 1934, 1484. We found the workup for the reduction of 2-methoxy-l-nitronaphthalene was simplified by replacing zinc with stannous chloride. See: Bellamy, F. D.; Ou, K. Tetrahedron Lett. 1984, 25, 839.
10. dba = dibenzylideneacetone. Ukai, T.; Kawazura, H.; Ishii, Y.; Bonnet, J. J.; Ibers, J. A. J. Organomet. Chem. 1974, 65, 253.