Efficient regioselective synthesis of enantiomerically pure 4- hydroxymethyl-Δ2-thiazoline

Tetrahedron Letters

Volumn 39, Issue 16, 1998, Pages 2293-2294

  Almqvist, Fredrik ^a,b   Guillaume, Dom ^a   Hultgren, Scott J ^b   Marshall, Garland R ^a  

^a Dept of Molec Biol and Pharmacol   (United States)

^b WASHINGTON UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PROPYLAMINE; THIAZOLE DERIVATIVE; THIOL DERIVATIVE;

ARTICLE; CHELATION; CHEMICAL REACTION; CYCLIZATION; ENANTIOMER; OPTICAL ROTATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOISOMERISM; SYNTHESIS;

EID: 0032537079     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00347-5     Document Type: Article

References (18)

1. 1. a) Jalal, M. A.; Hossain, M. B.; Helm, D. V.; Snaders-Loehr, J.; Actis, L. A.; Crosa, J. H. J. Am. Chem. Soc. 1989, 111, 292-296.
2. b) Dreschel, H.; Stephan, H.; Lotz, R.; Haag, H.; Hantke, K.; Jung, G. Liebigs Ann. 1995, 1727-1733.
3. c) Gerwich, W. H.; Proteau, P. J.; Nagle, D. G.; Hamel, E.; Blokhin, A.; Slate, D. L. J. Org. Chem. 1994, 59, 1243-1245.
4. d) Nagle, D. G.; Geralds, R. S.; Yoo, H.-D.; Gerwich, W. H.; Kim, T.-S.; Nambu, M.; White, J. D. Tetrahedron Lett. 1995, 36, 1189-1192.
5. 2. a) Handrick, G. R.; Atkinson, E. R.; Granchelli, F. E.; Bruni, R. J. J. Med. Chem. 1965, 8, 762-766.
6. b) Hoveyda, H. R.; Karunaratne, V.; Orvig, C. Tetrahedron 1992, 48, 5219-5226.
7. 3. a) Schmitz, W. D.; Romo, D. Tetrahedron Lett. 1996, 37, 4857-4860.
8. b) Fantin, G.; Fogagnolo, M.; Medici, A.; Pedrini, P. Heterocycles 1993, 36, 473-484.
9. 4. a) Ito, Y.; Ito, I; Hirao, T.; Saegusa, T. Synthetic Commun. 1974, 4, 97-103.
10. b) Ito, Y.; Inubushi, Y.; Zenbayashi, M.; Tomita, S.; Saegusa, T. J. Am. Chem. Soc. 1973, 95, 4447-4448.
11. 5. Meyers, A. I.; Knaus, G.; Kimata, K.; Ford, M. E. J. Am. Chem. Soc. 1976, 98, 567-576.
12. 6 . Meyers, A. I.; Whitten, C. E. Heterocycles 1976, 10, 1687-1692.
13. 7. Nagao, Y.; Kumagai, T.; Takao, S.; Abe, T.; Ochiai, M.; Inoue, Y.; Taga, T.; Fujita, E. J. Org. Chem. 1986, 51, 4739-4741. No physico-chemical data were included to assess the optical purity of the thiazoline.
14. 8. Wenker, H. J. Am. Chem. Soc. 1935, 57, 1079-1080.
15. 9 . Vorbruggen, H.; Krolikiewicz, K. Tetrahedron 1993, 49, 9353-9372.
16. 3-THF. For other non racemizing methods see: Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-875.
17. 3 solution. After evaporation of the organic phase, the thiazoline was purified by chromatography if necessary.
18. 3, 75 MHz) δ: 170.5, 159.5, 77.7, 61.7, 33.0, 13.8.