Highly enantioselective synthesis of 3-hydroxy-2-phenylpiperidine via the sharpless AD-reaction

Heterocycles

Volumn 51, Issue 5, 1999, Pages 1067-1071

  Stadler, Heinz ^a   Bös, Michael ^a,b  

^a F HOFFMANN LA ROCHE LTD   (Switzerland)

^b BOEHRINGER INGELHEIM CANADA LTD   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

3 HYDROXY 2 PHENYLPIPERIDINE; HETEROCYCLIC COMPOUND; NEUROKININ 1 RECEPTOR ANTAGONIST; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CIS ISOMER; DIASTEREOISOMER; DRUG SYNTHESIS; HYDROGENATION; HYDROLYSIS; HYDROXYLATION; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0344980248     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-99-8489     Document Type: Article

References (11)

1. C. J. Swain, in Progress in Medicinal Chemistry, Vol. 35, 1998, 57.
2. T. Harrison, B. J. Williams, C. J. Swain, and R. G. Ball, Bioorg. Med. Chem. Lett., 1994, 4, 2545.
3. J.J. Hale, S. G. Mills, M. MacCoss, S. K. Shah, H. Qi, D. J. Mathre, M. A. Cascieri, S. Sadowski, C. D. Strader, D. E. MacIntyre, and J. M. Metzger, J. Med. Chem., 1996, 39, 1760.
4. M. S. Ashwood, I. F. Cottrell, and A. J. Davies, Tetrahedron: Asymmetry, 1997, 8, 957.
5. R. Baker, T. Harrison, C. J. Swain, and B. J. Williams, European Patent Application 0 528 495 A1 (Chem. Abstr., 1993, 119, 177 122).
6. a) Z.-M. Wang, X.-L. Zhang, and K. B. Sharpless, Tetrahedron Lett., 1992, 33, 6407;
7. b) T. J. Hodgkinson and M. Shipman, Synthesis, 1998, 1141.
8. T. Hashiyama, K. Morikawa, and K. B. Sharpless, J. Org. Chem., 1992, 57, 5067.
9. M. Vaultier, P. H. Lambert, and R. Carrié, Bull. Soc. Chim. Fr., 1986, 83.
10. R. E. Ireland, R. H. Müller, and A. K. Willard, J. Am. Chem. Soc., 1986, 98, 2868.
11. Ph. Cazeau, F. Moulines, O. Laporte, and F. Duboudin, J. Organomet. Chem., 1989, 201, C9.