The synthesis of enantiomerically pure, highly functionalized heterocycles: The products of amino acid based acylnitroso hetero Diels-Alder reactions[1]

Enantiomer

Volumn 2, Issue 5, 1997, Pages 367-380

  Vogt, Paul F ^a   Miller, Marvin J ^a   Mulvihill, Mark J ^a   Ramurthy, Savithri ^a   Savela, Gordon C ^a   Ritter, Allen R ^a  

^a UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

Chiral Acylnitroso Dieneophiles; Diastereoselectivity; Enantiomerically Pure Heterocycles; Hetero Diels Alder Cycloaddition; Optically Pure Hydroxamic Acids

Indexed keywords

AMINO ACID; HETEROCYCLIC COMPOUND; HYDROXAMIC ACID; NITROSO DERIVATIVE;

ARTICLE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

AMINO ACIDS; HETEROCYCLIC COMPOUNDS; HYDROXAMIC ACIDS; NITROSO COMPOUNDS; STEREOISOMERISM;

EID: 0031306301     PISSN: 10242430     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (25)

1. Results presented, in part, at the 29th Great Lakes Meeting of the American Chemical Society, Normal, IL, May 1996, Program and Abstracts, 107,
2. and at the 210th National Meeting American Chemical Society, Chicago, IL, August 1995, Program and Abstracts, 68.
3. (a) Waldmann H., Synthesis, 1994, 535.
4. (b) Streith J. and Defoin A., Synthesis, 1994, 1107.
5. Ritter A.R. and Miller M.J., J. Org. Chem., 1994, 59, 4602.
6. The enantiomeric purity was determined, after N-O bond reduction of the cycloadducts, by Pirkle column HPLC analysis on the corresponding 3,5-dinitrobenzoylated cis-aminocyclopentanol derivatives.
7. Ritter A.R. and Miller M.J., Tetrahedron Lett., 1994, 35, 9379.
8. Ghosh A., Ritter A.R. and Miller M.J., J. Org. Chem., 1995, 60, 5808.
9. Ghosh A. and Miller M.J., Tetrahedron Lett., 1995, 36, 6399.
10. Strieth J., Defoin A. and Brouilliard-Poichet A., Tetrahedron Lett., 1989, 30, 7061.
11. Miller M.J., Mattingly P.G., Morrison M.A. and Kerwin J.F., J. Am. Chem Soc., 1980, 102, 7026.
12. Basha A., Lipton M. and Weinreb S.M., Tetrahedron Lett., 1977, 48, 4174.
13. Garner P. and Park J.M., J. Org. Chem., 1987, 52, 2361.
14. Pirrung M.C. and Chau J.H.-L., J. Og. Chem., 1995, 60, 8084.
15. (a) Miller M.J., Biswas A. and Krook M.A., Tetrahedron, 1983, 39, 2571.
16. (b) Fishbein W.N., Daly J. and Streeter C.L., Anal. Biochem., 1969, 28, 13.
17. (a) Miller A., MacPaterson T. and Procter G., Synlett, 1989, 1, 32.
18. (b) Miller A. and Procter G., Tetrahedron Lett., 1990, 31, 1041.
19. (c) Miller A. and Procter G., Tetrahedron Lett., 1990, 31, 1043.
20. Using the L-series of amino acids, when diastereoselectivity was observed, the lower numbered diastereomer was the major diastereomer.
21. Mancuso A.J. and Swern D., Synthesis, 1981, 165.
22. Aldehyde formation was checked by the Purpald® test: Durst H.D. and Gokel G.W., J. Chem. Ed., 1978, 55, 206.
23. The acylnitroso species is known to be very electrophilic as well as dieneophilic: Kirby G. W., Chem. Soc. Rev., 1977, 1.
24. Teng M. and Miller M.J., J. Am. Chem. Soc., 1993, 115, 548.
25. Ramasamy K., Olsen R.K. and Emery T., J. Org. Chem., 1981, 46, 5438.