Theoretical studies of [2,3]-sigmatropic rearrangements of allylic selenoxides and selenimides

Molecules

Volumn 14, Issue 9, 2009, Pages 3229-3236

  Bayse, Craig A ^a   Antony, Sonia ^a  

^a OLD DOMINION UNIVERSITY   (United States)

Author keywords

2,3 sigmatropic rearrangements; Density functional theory; Selenium; Selenoxides

Indexed keywords

ALLYL COMPOUND; SELENIUM DERIVATIVE;

ARTICLE; CHEMICAL MODEL; CHEMISTRY; CONFORMATION;

ALLYL COMPOUNDS; MODELS, CHEMICAL; MOLECULAR CONFORMATION; SELENIUM COMPOUNDS;

EID: 70349491987     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules14093229     Document Type: Article

References (24)

1. Nishibatashi, Y.; Uemura, S. Sigmatropic rearrangements of organoselenium compounds. In Organoselenium Chemistry. A Practical Approach; Back, T.G, Ed.; Oxford University Press: Oxford, UK, 1999; pp. 207-221.
2. Zanoni, G.; Castronovo, F.; Perani, E.; Vidari, G. A, J prostaglandin swap: A new tactic for cyclopentenone prostaglandin synthesis. J. Org. Chem. 2003, 68, 6803-6805.
3. Davoren, J.E.; Harcken, C.; Martin, S.F. Enantioselective synthesis and structure revision of solandelactone E. J. Org. Chem. 2008, 73, 391-402.
4. Back, T.G.; McPhee, D.J. A caveat concerning the use of N-(phenylseleno)phthalimide and tri-n-butylphosphine for the conversion of alcohols to selenides. Formation of 3-phthalimido derivatives from an allylic 3-sterol. J. Org. Chem. 1984, 49, 3842-3843.
5. Shea, R.G.; Fitzner, J.N.; Fankhauser, J.E.; Spaltenstein, A.; Carpino, P.A.; Peevey, R.M.; Pratt, D.V.; Tenge, B.J.; Hopkins, P.B. Allylic selenides in organic synthesis: New methods for the synthesis of allylic amines. J. Org. Chem. 1986, 51, 5243-5252.
6. Peng, X.; Hong, I.S.; Li, H.; Seidman, M.M.; Greenberg, M.M. Intrastrand cross-link formation in duplex and triplex DNA by modified pyrimidines. J. Am. Chem. Soc. 2008, 130, 10299-10306.
7. Davis, F.A.; Reddy, R.T. Asymmetric oxidation of simple selenides to selenoxides in high enantiopurity. Stereochemical aspects of the allylic selenoxide/allyl selenenate rearrangement. J. Org. Chem. 1992, 57, 2599-2606.
8. Nishibayashi, Y.; Singh, J.D.; Fukuzawa, S.; Uemura, S. Synthesis of [R,S;R,S]-and [S,R,S,R]-bis[2-[1-(dimethylamino)ethyl]ferrocenyl] diselenides and their application to asymmetric selenoxide elimination and [2,3]sigmatropic rearrangement. J. Org. Chem. 1995, 60, 4114-4120.
9. Reich, H.J.; Yelm, K.E. Asymmetric induction in the oxidation of [2.2]paracyclophane-substituted selenides. Application of chirality transfer in the selenoxide [2,3] sigmatropic rearrangement. J. Org. Chem. 1991, 56, 5672-5679.
10. Soma, T.; Shimizu, T.; Hirabayashi, K.; Kamigata, N. Stabilizing effect of intramolecular Lewis base toward racemization of optically active selenoxides. Heteroatom Chem. 2007, 18, 301-311.
11. Fankhauser, J.E.; Peevey, R.M.; Hopkins, P.B. Synthesis of protected allylic amines from allylic phenyl selenides: Improved conditions for the chloramine T oxidation of allylic phenyl selenides. Tetrahedron Lett. 1984, 25, 15-18.
12. Shea, R.G.; Fitzner, J.N.; Fankhauser, J.E.; Hopkins, P.B. Direct conversion of allylic selenides to protected allylic amines. J. Org. Chem. 1984, 49, 3647-3650.
13. Shea, R.G.; Fitzner, J.N.; Fankhauser, J.E.; Spaltenstein, A.; Carpino, P.A.; Peevey, R.M.; Pratt, D.V.; Tenge, B.J.; Hopkins, P.B. Allylic selenides in organic synthesis: New methods for the synthesis of allylic amines. J. Org. Chem. 1986, 51, 5243-5252.
14. Reich, H.J.; Yelm, K.E.; Wollowitz, S. Kinetics, thermodynamics, and stereochemistry of the allyl sulfoxide-sulfenate and selenoxide-selenenate [2,3] sigmatropic rearrangements. J. Am. Chem. Soc. 1983, 105, 2503-2504.
15. Freeman, F.; Bathala, R.M.; Cavillo, J.E.; Huang, A.C.; Jackson, T.K.; Lopez-Mercado, A.Z.; Phung, S.; Suh, J.; Valencia, D.O. [2,3]-sigmatropic rearrangements of hydrogen and alkyl 3-propenyl sulfoxides: A computational study. Intern. J. Quant. Chem. 2006, 106, 2390-2397.
16. Bayse, C.A.; Allison, B.D. Activation energies of selenoxide elimination from Se-substituted selenocysteine. J. Mol. Model. 2007, 13, 47-53.
17. Macdougall, P.E.; Smith, N.A.; Schiesser, C.H. Substituent effects in selenoxide elimination chemistry. Tetrahedron 2008, 64, 2824-2831.
18. Bayse, C.A.; Baker, R.A.; Ortwine, K.N. Relative strengths of Se-N,O interactions: Implications for glutathione peroxidase activity. Inorg. Chim. Acta 2005, 358, 3849-3854.
19. PQS Version 3.3. Parallel Quantum Solutions: Fayetteville, AR, USA.
20. Dunning, T.H. Gaussian basis functions for use in molecular calculations. III. Contraction of (10s6p) atomic basis sets for the first row atoms. J. Chem. Phys. 1971, 55, 716-723.
21. Hurley, M.M.; Pacios, L.F.; Christiansen, P.A.; Ross, R.B.; Ermler, W.C. Ab initio relativistic effective core potentials with spin-orbit operators. II. K through Kr. J. Chem. Phys. 1986, 84, 6840-6853.
22. Wadt, W.R.; Hay, P.J. Ab initio effective core potentials for molecular calculations. Potentials for main group elements Na to Bi. J. Chem. Phys. 1985, 82, 284-298.
23. Dunning, T.H. Gaussian basis functions for use in molecular calculations. I. Contraction of (9s5p) atomic basis sets for the first-row atoms. J. Chem. Phys. 1970, 53, 2823-2833.
24. Bayse, C.A.; Antony, S. Molecular modeling of bioactive selenium compounds. Main Group Chem. 2007, 6, 185-200.