re- and si-face-selective nitroaldol reactions catalyzed by a rigid chiral quaternary ammonium salt: A highly stereoselective synthesis of the HIV protease inhibitor amprenavir (Vertex 478)

Angewandte Chemie - International Edition

Volumn 38, Issue 13-14, 1999, Pages 1931-1934

  Corey, E J ^a   Zhang, Fu Yao ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

Amino alcohols; Chiral auxillaries; Diastereoselectivity; Nitroaldol reaction; Phase transfer catalysis

Indexed keywords

AMMONIUM DERIVATIVE; AMPRENAVIR; PROTEINASE; PROTEINASE INHIBITOR;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033549552     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19990712)38:13/14<1931::AID-ANIE1931>3.0.CO;2-4     Document Type: Article

References (23)

1. C. Flexner, New Eng. J. Med. 1998, 338, 1281-1292.
2. M. L. West, D. P. Fairlie, Trends Pharm. Sci. 1995, 16, 67-74.
3. D. Lednicer, The Organic Chemistry of Drug Synthesis, Vol. 6, Wiley, New York, 1999, Chap. 1, pp. 1-32.
4. N. Shibata, T. Katoh, S. Terashima, Tetrahedron Lett. 1997, 38, 619-620, and references therein.
5. E. E. Kim, C. T. Baker, M. D. Dwyer, M. A. Murcko, B. G. Rao, R. D. Tung, M. A. Navia, J. Am. Chem. Soc. 1995, 117, 1181-1182.
6. R. D. Tung, M. A. Murcko, G. R. Bhisetti, Vertex Pharmaceuticals, Inc. WO94/05639 1994.
7. a) Personal communication from Dr. J. D. Wilson, Director of Process Chemistry, Vertex Pharmaceuticals, Inc.;
8. b) see also P. Chen, P. T. W. Cheng, M. Alam, B. D. Beyer, G. S. Bisacchi, T. Dejneka, A. J. Evans, J. A. Greytok, M. A. Hermsmeier, W. Griffith Humphreys, G. A. Jacobs, O. Kocy, P.-F. Lin, K. A. Lis, M. A. Marella, D. E. Ryono, A. K. Sheaffer, S. H. Spergel, C-q. Sun, J. A. Tino, G. Vite, R. J. Colonno, R. Zahler, J. C. Barrish, J. Med. Chem. 1996, 39, 1991-2007;
9. c) A. K. Ghosh, J. F. Kincaid, W. Cho, D. E. Walters, K. Krishnan, K. A. Hussain, Y. Koo, H. Cho, C. Rudall, L. Holland, J. Buthod, Bioorg. Med. Chem. Lett. 1998, 8, 687-690.
10. a) M. T. Reetz, Angew. Chem. 1991, 103, 1559-1573; Angew. Chem. Int. Ed. Engl. 1991, 30, 1531-1546;
11. a) M. T. Reetz, Angew. Chem. 1991, 103, 1559-1573; Angew. Chem. Int. Ed. Engl. 1991, 30, 1531-1546;
12. b) M. T. Reetz, M. W. Drewes, A. Schmitz, Angew. Chem. 1987, 99, 1186-1188; Angew. Chem. Int. Ed. Engl. 1987, 26, 1141-1143;
13. b) M. T. Reetz, M. W. Drewes, A. Schmitz, Angew. Chem. 1987, 99, 1186-1188; Angew. Chem. Int. Ed. Engl. 1987, 26, 1141-1143;
14. c) S. Hanessian, P. V. Devasthale, Tetrahedron Lett. 1996, 37, 987-990;
15. 3N in dimethyl sulfoxide at 10°C (97%).
16. a) E. J. Corey, F. Xu, M. C. Noe, J. Am. Chem. Soc. 1997, 119, 12414-12415;
17. b) E. J. Corey, Y. Bo, J. Busch-Petersen, J. Am. Chem. Soc. 1998, 120, 13000-13001;
18. c) E. J. Corey, M. C. Noe, F. Xu, Tetrahedron Lett. 1998, 39, 5347-5350.
19. -) to afford the corresponding quaternary ammonium hydroxide followed by treatment with one equivalent of HF and removal of solvent in vacuo. The quaternary ammonium salt may be separated from the nitro alcohol 5 for reuse by selectively dissolving the latter in diethyl ether.
20. For diastereoselective nitroaldol reactions catalyzed by rare earth-Li-BINOL complexes, see H. Sasai, W.-S. Kim, T. Suzuki, M. Shibasaki, Tetrahedron Lett. 1994, 35, 6123-6126.
21. This amino alcohol possessed identical properties to those previously reported: J. S. Ng, C. A. Przybyla, C. Liu, J. C. Yen, F. W. Muellner, C. L. Weyker, Tetrahedron 1995, 51, 6397-6410.
22. The allyl ether quaternary ammonium salt 9 afforded somewhat better stereoselectivity in this reaction than did the benzyl ether analogue 4, Bromide 9 is converted into the corresponding fluoride in situ.
23. [7b] and spectral data.