Asymmetric synthesis of 1,3-oxazolidines from chiral imines using Rh(III) catalyst

Bulletin of the Korean Chemical Society

Volumn 26, Issue 2, 2005, Pages 225-226

  Lee, Seung Han ^a   Kim, Young Hwan ^a  

^a Kyung Hee University   (South Korea)

Author keywords

1,2 Amino alcohols; 1,3 Oxazolidines; Asymmetric synthesis; Rhodium catalyst

Indexed keywords

ACETONE; AMINOALCOHOL; DIAZOACETIC ACID ETHYL ESTER; IMINE; OXAZOLIDINE DERIVATIVE; RHODIUM;

ADDITION REACTION; ARTICLE; ASYMMETRIC SYNTHESIS; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; DEBENZYLATION; ELECTRON TRANSPORT; HYDROGENOLYSIS; HYDROLYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REPRODUCIBILITY; STEREOCHEMISTRY; TECHNIQUE; TEMPERATURE DEPENDENCE;

EID: 14844297714     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: 10.5012/bkcs.2005.26.2.225     Document Type: Article

References (19)

1. (a) Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835.
2. (b) Gordon, K.; Bolger, M.; Khan, N.; Balasubramanian, S. Tetrahedron Lett. 2000, 41, 8621.
3. (c) Prasad, K. R. K.; Joshi, N. N. J. Org. Chem. 1997, 62, 3770.
4. (d) Dai, W.-M.; Zhu, H. J.; Hao, X.-J. Tetrahedron: Asymmetry 1996, 7, 1245.
5. (e) Heaney, H.; Papageorgiou, G.; Wilkins, R. F. Tetrahedron 1997, 53, 14381.
6. (f) Le Bail, M.; Perard, J.; Aitken, D. J.; Bonin, M.; Husson, H.-P. Tetrahedron Lett. 1997, 38, 7177.
7. Lee, S.-H.; Yang, J.; Han, T.-D. Tetrahedron Lett. 2001, 42, 3487.
8. (a) Hansen, K. B.; Finney, N. S.; Jacobsen, E. N. Angew. Chem. Int. Ed. Engl. 1995, 34, 676.
9. (b) Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M. J. Am. Chem. Soc. 1993, 115, 5328.
10. Acetone distilled from molecular sieve under nitrogen was used.
11. 3) δ 168.30, 149.63, 147.13, 144.27, 129.23, 128.03, 127.52, 127.12, 122.75, 97.51, 77.21, 64.82, 60.87, 56.85, 28.89, 22.50, 21.70, 13.69.; Anal, calcd: C, 66.32; H, 6.58; N, 7.03. Found C, 66.50; H, 6.73; N, 7.07.
12. Xie, W.; Fang, J.; Wang, P. G. Tetrahedron 1999, 55, 12929.
13. Park, C. S.; Choi, H. G.; Lee, H. J.; Lee, W. G.; Ha, H. J. Tetrahedron: Asymmetry 2000, 11, 3283.
14. Chang, J.-W.; Bae, J. H.; Shin, S.-H.; Park, C. S.; Choi, D.; Lee, W. K. Tetrahedron Lett. 1998, 39, 9193.
15. (a) Doyle, M. P.; Van, M.; Hu, W.; Gronenberg, L. S. J. Am. Chem. Soc. 2003, 125, 4692.
16. (b) Rasmussen, K. G.; Jørgensen, K. A. J. Chem. Soc. Perkin Trans, 1 1997, 1287.
17. (a) Hodgson, D. M.; Pierard, F. Y. T. M.; Stupple, P. A. Chem. Soc. Rev. 2001, 30, 50.
18. (b) Doyle, M. P.; Hu, W.; Timmons, D. J. Org. Lett. 2001, 3, 933.
19. (c) Doyle, M. P.; Forbes, D. C.; Protopopova, M. N.; Stanley, S. A.; Vasbinder, M. M.; Xavier, K. R. J. Org. Chem. 1997, 62, 7210.