Highly regioselective opening of optically active N-Boc-2,3-aziridino alcohol derivatives with metal halides

Tetrahedron Letters

Volumn 39, Issue 16, 1998, Pages 2385-2388

  Righi, Giuliana ^a   Franchini, Tiziana ^a   Bonini, Carlo ^b  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b UNIVERSITY OF BASILICATA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; AZIRIDINE DERIVATIVE; HALIDE; METAL;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; STEREOCHEMISTRY;

EID: 0032537156     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00204-4     Document Type: Article

References (25)

1. 1 Bonini, C.; Righi, G.; D'Achille, R. Tetrahedron Lett. 1996, 37, 6893. For related previous work on 2,3-epoxy alcohols and α,β-epoxy esters see also ref. 10.
2. 2 See review : a) Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835. for most recent and significant papers see:
3. b) Barrett, A. G. M; Seefeld, M. A.; White, A. J. P.; Williams, D. J. J. Org. Chem. 1996, 61, 2677.
4. c) Castejon, P.; Moyano, A.; Pericas, M. A.; Riera, A. Tetrahedron 1996, 52, 7063.
5. 3 Tanner, D.; He, H. M.; Somfai, P. Tetrahedron 1992, 48, 6069.
6. 4 Tanner, D.; Gaurun, O. R. Tetrahedron 1995, 51, 8279.
7. 5 See review on the preparation and reactions of aziridines :Tanner, D., Angew. Chem. Int. Ed. Engl. , 1994, 33, 599 and references therein.
8. 6 Protective groups in Organic Synthesis Green, T. W.; Wuts, P. G. M.; John Wiley & Sons, Inc. 1991, pg 317 and 379.
9. 7 See for some selected examples: a) Satake, A.; Shimizu, I.; Yamamoto, A. Synlett 1995, 64.
10. b) Ezquerra, J.; Pedregal, C.; Lamas, C. Tetrahedron Lett. 1996, 37, 683.
11. c) McCort, I.; Dureault, A.;Depezay, J. Tetrahedron Lett. 1996, 37, 7717.
12. d) Funaki, I.; Thijs, L.; Zwanenburg, B. Tetrahedron 1996, 52, 9909.
13. 8 During the preparation of the manuscript we have been made aware of the use of the nosyl N-protecting group in the nucleophilic opening of 1,2-aziridines (Maligres, P. E.; See, M. M.; Askin, D.; Reider, P. J. Tetrahedron Lett. 1991, 38, 5253).
14. 9. Also crude aziridine-2-carboxylates (prepared from the corresponding optically active α,β-epoxy esters according to Legters, J.; Thijs, L.; Zwanenburg, B. Recl. Trav. Chim. Pays-Bas 1992, 111,), can be easily protected to the corresponding N-BOC derivatives and easily purified by flash chromatography .
15. 10. For related previous opening of 2,3-epoxy alcohols and esters with metal halides see a) Bonini, C.; Righi, G. Review: Synthesis 1994, 3, 225.
16. b) Bonini, C.; Chiummiento, L.; Federici, C.; Funicello, M.; Righi, G.; Rossi, L. Tetrahedron Lett. 1994, 35, 797.
17. c) Bonini, C.; Federici, C.; Righi, G.; Rossi, L. J. Org. Chem. 1995, 60, 4803.
18. d) Bonini, C.; Righi, G.; Rumboldt, G. Tetrahedron 1995, 51, 13401.
19. e) Bonini, C.; Righi, G.;Rumboldt, G. J. Org. Chem. 1996, 61, 3557.
20. 13C-NMR for determining the regio and diastereomeric ratio.
21. 2 the best reagent for an excellent C-3 attack, with regio and chemical yields compared to those reported in Table 1.
22. 13. The reaction was also performed on two model N-Boc protected aziridino-2-carboxylates affording the corresponding N-Boc-α-amino-β-bromo esters in the same excellent regiochemicai yields (unpublished results).
23. 14. Chatgilialoglu, C. Acc. Chem. Res. 1992, 25, 188.
24. 5 (75% and 40% yield respectively).
25. 4, evaporated in vacuo and purified by flash chromatography afforded the N-Boc-amino alcohol.