Enantioselective synthesis of α,β-disubstituted-β-amino acids

Journal of the American Chemical Society

Volumn 125, Issue 39, 2003, Pages 11796-11797

  Sibi, Mukund P ^a   Prabagaran, Narayanasamy ^a   Ghorpade, Sandeep G ^a   Jasperse, Craig P ^a  

^a NORTH DAKOTA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BETA AMINO ACID;

AMINO ACID METABOLISM; ANALYTIC METHOD; ARTICLE; CHIRALITY; DERIVATIZATION; ELECTRON TRANSPORT; ENANTIOMER; ENANTIOSELECTIVITY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STRAIN DIFFERENCE; SYNTHESIS;

AMINO ACIDS; HYDROXYLAMINES; IMIDES; ISOXAZOLES; STEREOISOMERISM;

EID: 0141732263     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0372309     Document Type: Article

References (20)

1. For a recent review on synthesis, see: Liu, M.; Sibi, M. P. Tetrahedron 2002, 58, 7991.
2. (a) Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959.
3. (b) Wenzel, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 12964.
4. (c) Horstmann, T. E.; Guerin, D. J.; Miller, S. J. Angew. Chem., Int. Ed. 2000, 39, 3635.
5. (d) Falborg, L.; Jørgensen, K. A. J. Chem. Soc., Perkin Trans. 1 1996, 2823.
6. (e) Doi, H.; Sakai, T.; Iguchi, M.; Yamada, K.; Tomioka, K. J. Am. Chem. Soc. 2003, 125, 2886.
7. (f) Sibi, M. P.; Shay, J. J.; Liu, M.; Jasperse, C. P. J. Am. Chem. Soc. 1998, 120, 6615.
8. (g) Sibi, M. P.; Asano, Y. J. Am. Chem. Soc. 2001, 123, 9708.
9. Ulongamides A.-F.; (a) Luesch, H.; Williams, P. G.; Yoshida, W. Y.; Moore, R. E.; Paul, V. J. J. Nat. Prod. 2002, 65, 996.
10. Dolastatins 11 and 12; (b) Pettit, G. R.; Kamano, Y.; Kizu, H.; Dufresne, C.; Herald, C. L.; Bontems, R.; Schmidt, J. M.; Boettner, F. E.; Nieman, R. A. Heterocycles 1989, 28, 553.
11. Majusculamide C: (c) Mynderse, J. S.; Hunt, A. H.; Moore, R. E. J. Nat. Prod. 1988, 51, 1299.
12. (a) Sibi, M. P.; Liu, M. Org. Lett. 2000, 2, 3393.
13. (b) Sibi, M. P.; Liu, M. Org. Lett. 2001, 3, 4181.
14. For mechanistic information, see: (c) Niu, D.; Zhao, K. J. Am. Chem. Soc. 1999, 121, 2456.
15. (d) Moglioni, A.; Muray, E.; Castillo, J. A.; Alvarez-Larena, A.; Moltrasio, G. Y.; Branchadell, V.; Ortuño, R. M. J. Org. Chem. 2002, 67, 2402.
16. Sibi, M. P.; Sausker. J. B. J. Am. Chem. Soc. 2002, 124, 984.
17. Goodman, S. N.; Jacobsen, E. N. Adv. Synth. Catal. 2002, 344, 953.
18. Metal triflimides have seen limited use in chiral catalysis. They possess several important properties such as solubility in nonpolar organic solvents, stability, and good Lewis acidity. Several other Lewis acids and ligands have also been examined in conjugate amine additions. These results will be reported in a full account.
19. Sibi, M. P.; Chen, J. J. Am. Chem. Soc. 2001, 123, 9472.
20. Ishikawa, T.; Nagai, K.; Kudoh, T.; Saito, S. Synlett 1995, 1171.