Stereochemical aspects of the Beckman rearrangement of oximes of levoglucosenone and its dihydro derivative. Enantioselective synthesis of (+)-γ-pelargonolactone

Chemistry of Natural Compounds

Volumn 39, Issue 6, 2003, Pages 563-568

  Valeev, F A ^a   Gorobets, E V ^a   Tsypysheva, I P ^a   Singizova, G Sh ^a   Kalimullina, L Kh ^b   Safarov, M G ^b   Shitikova, O V ^a   Miftakhov, M S ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

^b Birsk Branch of Federal State Budgetary Educational Establishment of Higher Education Bashkir State University   (Russian Federation)

Author keywords

Ketoximes; Levoglucosenone; Nitriles; Nucleophilic substitution; Second order Beckman rearrangement

Indexed keywords

CURCULIONIDAE; ZEA MAYS;

EID: 3342895856     PISSN: 00093130     EISSN: None     Source Type: Journal    
DOI: 10.1023/B:CONC.0000018110.36123.f2     Document Type: Article

References (6)

1. F. A. Valeev, I. N. Gaisina, L. V. Spirikhin, and M. S. Miftakhov, Izv. Akad. Nauk, Ser. Khim., 3, 549 (1997).
2. H. P. Fischer, C. A. Grob, and E. Renk, Helv. Chim. Acta, 45, 2539 (1962).
3. G. A. Olan, Y. D. Vankar, and A. L. Berrier, Synthesis, 7, 45 (1980).
4. F. A. Valeev, E. V. Gorobets, and M. S. Miftakhov, Zh. Org. Khim., 34, No. 6, 937 (1998).
5. J. Cardellach, J. Fond, and R. M. Ortuno, Heterocycl. Chem., 21, 327 (1984).
6. J. P. Vigneron, R. Meric, M. Larcheveque, A. Debal, and J. Y. Lallemand, Tetrahedron, 40, 3521 (1984).