Reductive cyclization of δ-hydroxy nitriles: A new synthesis of glycosylamines

Organic Letters

Volumn 5, Issue 18, 2003, Pages 3237-3239

  Dorsey, Andrew D ^a   Barbarow, Jennifer E ^a   Trauner, Dirk ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; AMINOSUGAR; NITRILE;

ARTICLE; CYCLIZATION; STEREOCHEMISTRY; SYNTHESIS;

ACETALS; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; GLYCOPEPTIDES; HEXOSAMINES; MOLECULAR STRUCTURE; NITRILES; OXIDATION-REDUCTION; STEREOISOMERISM;

EID: 0141856297     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035111s     Document Type: Article

References (17)

1. (a) Dwek, K. Chem. Rev. 1996, 96, 683.
2. (b) Arsequell, G.; Valencia, G. Tetrahedron: Asymmetry 1999, 10, 3045.
3. (c) Grogan, M. J.; Pratt, M. R.; Marcaurelle, L. A.; Bertozzi, C. R. Annu. Rev. Biochem. 2002, 71, 593.
4. (a) Ragan, J. A.; Claffey, M. C. Heterocycles 1995, 41, 57.
5. (b) Ennis, M. D.; Hoffman, R. L.; Ghazal, N. B.; Old, D. W.; Mooney, P. A. J. Org. Chem. 1996, 61, 5813.
6. Apparently, reactions of TMSCN and Meyers' lactams have not been reported. For a review of the chemistry of Meyers' lactams, see: Meyers, A. I.; Brengel, G. P. J. Chem. Commun. 1997, 1.
7. For examples, see: (a) Overman, L. E.; Ricca, D. J.; Tran, V. D. J. Am. Chem. Soc. 1993, 115, 2042. (b) Deprez, P.; Royer, J.; Husson, H.-P. Tetrahedron 1993, 49, 3781.
8. For examples, see: (a) Overman, L. E.; Ricca, D. J.; Tran, V. D. J. Am. Chem. Soc. 1993, 115, 2042. (b) Deprez, P.; Royer, J.; Husson, H.-P. Tetrahedron 1993, 49, 3781.
9. Aebischer, B.; Hanssen, H.; Vasella, A.; Schweizer, W. J. Chem. Soc., Perkin Trans. 1 1982, 6, 2139.
10. Ermert, P.; Vasella, A. Helv. Chim. Acta 1991, 74, 2043.
11. Heightman, T.; Ermert, P.; Klein, D.; Vasella, A. Helv. Chim. Acta 1995, 78, 514.
12. Yokoyama, M.; Irie, M.; Sujino, K.; Kagemoto, T.; Togo, H.; Funabashi, M. J. Chem. Soc., Perkin Trans. 1 1992, 16, 2127.
13. Attempts to prepare these imidates through acid- or base-mediated cyclizations of the corresponding hydroxynitriles failed.
14. Seyden-Peyne, J. Reductions by the Alumino- and Borohydrides in Organic Synthesis; VCH: New York, 1991; p 129.
15. Kozar, T.; Tvaroska, I. Biopolymers 1990, 29, 1531.
16. Torres, O. L.; Haro, I.; Bardaoi, E.; Valencia, G.; Garcia-Anton, O. M.; Reig, F. Tetrahedron 1988, 44, 6131.
17. Danishefsky, S.; Hu, S.; Cirillo, P.; Eckhardt, M.; Seeberger, P. Chem. Eur. J. 1997, 3, 1617.