(S)-tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo-[1,2-c][1,3,2]oxazaborole-borane complex

Organic Syntheses

Volumn 74, Issue , 1997, Pages 50-

  Xavier, Lyndon C ^b   Mohan, Julie J ^b   Mathre, David J ^b   Thompson, Andrew S ^b   Carroll, James D ^b   Corley, Edward G ^b   Desmond, Richard ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85026885785     PISSN: 00786209     EISSN: 16000730     Source Type: Book Series    
DOI: 10.15227/orgsyn.074.0050     Document Type: Article

References (35)

1. Marfey, P. Carlsberg Res. Commun. 1984, 49, 591–596.
2. Top, S.; Meyer, A.; Jaouen, G. Tetrahedron Lett. 1979, 3537–3540.
3. Kabuto, K.; Imuta, M.; Kempner, E. S.; Ziffer, H. J. Org Chem. 1978, 43, 2357–2361.
4. (a) Soai, K.; Ookawa, A.; Ogawa, K.; Kaba, T. J. Chem. Soc., Chem. Commun. 1987, 467–468;
5. Soai, K.; Ookawa, A.; Kaba, T.; Ogawa, K. J. Am. Chem. Soc. 1987, 109, 7111–7115.
6. (c) Takahashi, H.; Kawabata, A.; Higashiyama, K. Chem. Pharm. Bull. 1987, 35, 1604–1607.
7. (d) Kraatz, U. German Patent DE 3 609 152, 1987; Chem. Abstr. 1988, 108, 56111C;
8. Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. Soc. 1987, 109, 5551–5553;
9. Corey, E. J.; Shibata, S.; Bakshi, R. K. J. Org. Chem. 1988, 53, 2861–2863;
10. Corey, E. J.; Reichard, G. A. Tetrahedron Lett. 1989, 30, 5207–5210;
11. Corey, E. J.; Link, J. O. Tetrahedron Lett. 1989, 30, 6275–6278;
12. Corey, E. J.; Bakshi, R. K. Tetrahedron Lett. 1990, 31, 611–614;
13. Rama Rao, A. V.; Gurjar, M. K.; Sharma, P. A.; Kaiwar, V. Tetrahedron Lett. 1990, 31, 2341–2344;
14. Jones, T. K.; Mohan, J. J.; Xavier, L. C.; Blacklock, T. J.; Mathre, D. J.; Sohar, P.; Jones, E. T. T.; Reamer, R. A.; Roberts, F. E.; Grabowski, E. J. J. J. Org. Chem. 1991, 56, 763–769.
15. (a) Seebach, D.; Enders, D.; Renger, B. Chem. Ber. 1977, 110, 1852–1865;
16. Enders, D.; Pieter, R.; Renger, B.; Seebach, D. Org. Synth., Coll. Vol. VI 1988, 542–549.
17. 19).
18. Corey, E. J.; Bakshi, R. K.; Shibata, S.; Chen, C.-P.; Singh, V. K. J. Am. Chem. Soc. 1987, 109, 7925–7926;
19. (a) Roussel-UCLAF French Patent FR M3638, 1965; Chem. Abstr. 1969, 70, 106375m.
20. Kapfhammer, J.; Matthes, A. Z. physiol. Chem. 1933, 223, 43–52.
21. 10. It should be noted that 6–10 equiv of the Grignard reagent are required to drive this reaction to completion. Quenching the excess phenylmagnesium bromide affords benzene—an environmental and health hazard.
22. Enders, D.; Kipphardt, H.; Gerdes, P.; Brena-Valle, L. J.; Bhushan, V. Bull. Soc. Chim. Belg. 1988, 97 , 691–704.
23. Mathre, D. J.; Jones, T. K.; Xavier, L. C.; Blacklock, T. J.; Reamer, R. A.; Mohan, J. J.; Jones, E. T. T.; Hoogsteen, K.; Baum, M. W.; Grabowski, E. J. J. J. Org. Chem. 1991, 56, 751–762.
24. 20,21;
25. Blacklock, T. J.; Jones, T. K.; Mathre, D. J.; Xavier, L. C., U.S. Patent 5 039 802, 1991; Chem. Abstr. 1991, 115, 232503n;
26. Kerrick, S. T.; Beak, P. J. Am. Chem. Soc. 1991, 113, 9708–9710;
27. Nikolic, N. A.; Beak, P. Org. Synth., Coll. Vol. IX 1998, 391.
28. Mathre, D. J.; Thompson, A. S.; Douglas, A. W.; Hoogsteen, K.; Carroll, J. D.; Corley, E. G.; Grabowski, E. J. J. J. Org. Chem. 1993, 58, 2880–2888;
29. Blacklock, T. J.; Jones, T. K.; Mathre, D. J.; Xavier, L. C., U.S. Patent 5 189 177, 1993:
30. U.S. Patent 5 039 802; Chem. Abstr. 1991, 115, 232503n.
31. Corey, E. J.; Azimioara, M.; Sarsha, S. Tetrahedron Lett. 1992, 33, 3429–3430.
32. Itsuno, S.; Ito, K.; Hirao, A.; Nakahama, S. J. Chem. Soc., Chem. Commun. 1983, 469–470;
33. 19.
34. (c) Singh, V. K. Synthesis 1992, 605–617;
35. Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1992, 3, 1475–1504.