Regioselective nucleophilic ring opening of epoxides and aziridines derived from homoallylic alcohols

Tetrahedron

Volumn 53, Issue 47, 1997, Pages 16139-16146

  Tanner, David ^a   Groth, Thomas ^a  

^a TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE DERIVATIVE; EPOXIDE;

ARTICLE; DERIVATIZATION; ENZYME SUBSTRATE; EPOXIDATION; MOLECULAR INTERACTION; NONHUMAN; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030723242     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10053-9     Document Type: Article

References (16)

1. For leading references to ring opening of 2,3-epoxy alcohols by hydride and cuprate reagents, see: (a) Ma, P.; Martin, V. S.; Masamune, S.; Sharpless, K. B.; Viti, S. M. J. Org. Chem. 1982, 47, 1378.
2. (b) Finan, J. M.; Kishi, Y. Tetrahedron Lett. 1982, 23, 2719.
3. Viti, S. M. Tetrahedron Lett. 1982, 23, 4541 (hydrides),
4. Nagaoka, H.; Kishi, Y. Tetrahedron 1981, 37, 3873.
5. Lipshutz, B. H.; Sengupta, S. Organic Reactions ; Wiley: New York, 1992; vol. 41, ch. 2, pp. 135 - 631 (cuprates).
6. For references to ring opening of 2,3-aziridino alcohols by hydride and cuprate reagents, see: (a) Tanner, D.; Somfai, P. Tetrahedron Lett. 1987, 28, 1211.
7. (b) Tanner, D.; He, H. M.; Somfai, P. Tetrahedron 1992,48, 6069.
8. Tanner, D.; Gautun, O. R. Tetrahedron 1995, 51, 8279.
9. Ibuka, T.; Nakai, K.; Akaji, M.; Tamamura, H.; Fujii, N.; Yamamoto, Y. Tetrahedron 1996, 52, 11739.
10. For example, (a) via Sharpless asymmetric dihydroxylation (AD) of olefins followed by stereospecific transformation to chiral epoxides: Kolb, H. C.; Sharpless, K. B. Tetrahedron 1992, 48, 10515 and refs. therein,
11. (b) Stereospecific transformation of chiral epoxides to aziridines: Tanner, D. Angew. Chem. Int. Ed. Engl. 1994, 33, 599 and refs. therein.
12. From chiral cyclic sulfates (via Sharpless AD): Lohray, B. B.; Gao, Y.; Sharpless, K. B. Tetrahedron Lett. 1989, 30, 2623.
13. Sharpless asymmetric aminohydroxylation of olefins (followed by ring closure): Li, G.; Chang, H.-T.; Sharpless, K. B. Angew. Chem. Int. Ed. Engl. 1996, 35, 451.
14. (e) For a recent review on asymmetric synthesis of aziridines: Osborn, H. M. I.; Sweeney, J. Tetrahedron:Asymmetry 1997, 8, 1693.
15. Fisher, M. E.; Overman, L. E. J. Org. Chem. 1990, 55, 1447.
16. 2, Lindlar cat., hexane