Diastereoselective synthesis of 3-amino-1,2-diols by reductive alkylation of 2,3-dialkoxynitriles

Tetrahedron Letters

Volumn 41, Issue 14, 2000, Pages 2369-2372

  Hutin, Pierre ^a   Larchevêque, Marc ^a  

^a CNRS   (France)

Author keywords

Aminoalcohols; Cyanohydrins; Diastereoselection; Grignard reagents

Indexed keywords

AMINOALCOHOL; CYANOHYDRIN; HETEROCYCLIC NITRO COMPOUND; NITRILE; REAGENT;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIASTEREOISOMER; ENANTIOMER; STEREOCHEMISTRY; SYNTHESIS;

EID: 0343183009     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00202-1     Document Type: Article

References (26)

1. Kempf, D.; Sham, H. Curr. Pharm. Des. 1996, 2, 225-246.
2. Peterson, M. A.; Polt, R. J. Org. Chem. 1993, 58, 4309-4314 and references cited herein.
3. For some recent syntheses, see: Overhand, M.; Hecht, S. M. J. Org. Chem. 1994, 59, 4721-4722;
4. Veith, U.; Schwardt, O.; Jäger, V. Synlett 1996, 1181-1183;
5. Zanardi, F.; Battistini, L.; Nespi, M.; Rassu, G.; Spanu, P.; Cornia, M.; Casiraghi, G. Tetrahedron: Asymmetry 1996, 7, 1169-1180;
6. Hümmer, W.; Dubois, E.; Gracza, T.; Jäger, V. Synthesis 1997, 634-642;
7. Du Bois, J.; Tomooka, C. S.; Hong, J.; Carreira, E. M. J. Am. Chem. Soc. 1997, 119, 3179-3180.
8. Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599-619;
9. Rayner, C. Synlett 1997, 11-21.
10. Bloch, R. Chem. Rev. 1998, 98, 1407-1438 and references cited herein.
11. Krepski, L. R.; Jensen, K. M.; Heilmann, M.; Rasmussen, J. K. Synthesis 1986, 301-303;
12. Brussee, J.; Dofferhoff, F.; Kruse, C. G.; Van der Gen, A. Tetrahedron 1990, 46, 1653-1658;
13. Jackson, W. R.; Jacobs, H. A.; Jayatilafe, G. S.; Matthews, B. R.; Watson, K. G. Aust. J. Chem. 1990, 43, 2045-2062;
14. Effenberger, F.; Gutterer, B.; Ziegler, T. Liebigs Ann. Chem. 1991, 269-273;
15. Urabe, H.; Aoyama, Y.; Sato, F. J. Org. Chem. 1992, 57, 5056-5057.
16. Charette, A. B.; Mellon, C. Tetrahedron 1998, 54, 10 525-10 535.
17. Hutin, P.; Larchevêque, M. Synthesis, in press.
18. 2 figuring alkyl or aryl groups, is based on the vanadium-catalyzed cross-coupling of aldehydes with chiral α-amino aldehydes: Konradi, A. W.; Kemp, S. J.; Pedersen, S. F. J. Am. Chem. Soc. 1994, 116, 1316-1323.
19. Mead, K.; Macdonald, T. L. J. Org. Chem. 1985, 50, 422-424;
20. Jurczak, J.; Pikul, S.; Bauer, T. Tetrahedron 1986, 42, 447-488.
21. Olah, G. A.; Narang, S. C.; Fung, A. P.; Gupta, B. C. G. Synthesis 1980, 657-658;
22. Maetz, P.; Rodriguez, M. Tetrahedron Lett. 1997, 38, 4221-4222.
23. Hutin, P.; Petit, Y.; Larchevêque, M. Tetrahedron Lett. 1998, 39, 8277-8280.
24. It must be outlined that the Grignard reagents do not react with nitriles 1 in pure THF, a result which is perhaps due to the formation of agregates. The reaction is however possible in a 2:1 mixture of diethyl ether and THF.
25. 3), 28.99 (CH), 57.71 (CH-N), 79.28 (C), 83.04 (2×CH), 109.40 (C), 127.58 (2×CH), 128.28 (CH), 128.53 (2×CH), 139.18 (C), 155.73 (C).
26. The N-Boc amino esters were analyzed on a 25 m Chirasil-D-Val column (Chrompack) on which such compounds with L configuration are eluted in first.