Synthesis of enantiopure substituted aziridines by diastereoselective N- bromocyclization and nucleophile-mediated regioselective opening

Tetrahedron Letters

Volumn 39, Issue 30, 1998, Pages 5373-5374

  Agami, Claude ^a   Amiot, Franck ^a   Couty, François ^a   Dechoux, Luc ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE DERIVATIVE; BROMINE DERIVATIVE;

ARTICLE; BROMINATION; CHEMICAL REACTION; CHIRALITY; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

EID: 0032560769     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01109-5     Document Type: Article

References (11)

1. 1. For a recent review, see: Osborn, H.M.I.; Sweeney J. Tetrahedron Asym. 1997, 8, 1693-1715.
2. 2. Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599-619.
3. 3. Fort, S.; McCort, I.; Dureault, A.; Depezay, J.C. Synlett. 1997, 1235-1236. and references cited herein.
4. 4 For a review see Kasai, M.; Kono, M. Synlett. 1992, 778-790.
5. 13C NMR data showed that the formation of products 7 as well as the formation of products 8 were totally stereoselective.
6. 3, 62.5 MHz): 47.7, 49.7, 61.3, 76.2, 92.3, 126.4, 128.1, 128.6, 128.8, 135.6, 136.7, 166.7.
7. 7. Agami, C.; Couty, F.; Hamon, L.; Venier, O. J. Org. Chem. 1997, 62, 2106-2112.
8. 3, 62.5 MHz): 17.1, 43.8, 60.5, 62.0, 75.7, 94.8, 127.2, 127.4, 127.9, 128.5, 128.9, 138.8, 142.0, 159.4.
9. 9. We thank Dr. Louis Hamon who performed these calculations.
10. 10. See for instance: (a) Palomio, C; Oiarbide, M.; Gonzalez, A.; Garcia, J.M.; Berree, F.; Linden, A. Tetrahedron Lett. 1996, 37, 6931-6934.
11. (b) O'Brien, P.; Warren, S. Tetrahedron Lett. 1996, 37, 3051-3054.