Computational elucidation on regio- and stereoselectivity on glycosylation of alcohols by N-Cbz-imino glycal-derived allyl N-nosyl aziridines

Tetrahedron Letters

Volumn 53, Issue 48, 2012, Pages 6573-6576

  Da Silva, Alan Patrick ^a   Bagatin, Mariane Cristovão ^a   De Freitas Gauze, Gisele ^a   Basso, Ernani Abicht ^a  

^a STATE UNIVERSITY OF MARINGÁ   (Brazil)

Author keywords

1,4 Regioselectivity; Glycosylation; Stereoselectivity; Theoretical calculations; Transition states

Indexed keywords

ALCOHOL DERIVATIVE; AZIRIDINE DERIVATIVE; N CBZ IMINO GLYCAL DERIVED ALLYL N NOSYL AZIRIDINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DIASTEREOISOMER; GLYCOSYLATION; STEREOCHEMISTRY;

EID: 84867897163     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.09.099     Document Type: Article

References (7)

1. V. Di Bussolo, A. Fiasella, L. Favero, F. Bertolini, and P. Crotti Org. Lett. 11 2009 2675
2. A.P. Silva, G.F. Gauze, N.P. Coelho, C.C. Silva, and E.A. Basso Tetrahedron Lett. 52 2011 62
3. A.P. Silva, G.F. Gauze, T.A. Matias, V.R. Souza, T.C. Rozada, and E.A. Basso Tetrahedron Lett. 52 2011 5043
4. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, V.; Barone, V.; Mennucci, V.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery Jr., J. A.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Keith, T.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian, Inc., Wallingford, CT: 2010.
5. C. Lee, W. Yang, and R.G. Paar Phys. Rev. B 37 1988 785
6. A.D. Becke J. Chem. Phys. 98 1993 1372
7. S. Chiodo, N. Russo, and E. Sicilia J. Chem. Phys. 125 2006 104107