Electrophilic additions to a 2-methylenebicyclo[2.1.1]hexane system: Probing μ-face selectivity for electrostatic and orbital effects

Organic Letters

Volumn 4, Issue 14, 2002, Pages 2297-2300

  Mehta, Goverdhan ^a   Singh, S Robindro ^a   Balanarayan, P ^b   Gadre, Shridhar R ^b  

^a INDIAN INSTITUTE OF SCIENCE   (India)

^b UNIVERSITY OF PUNE   (India)

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ARTICLE;

EID: 0037939452     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026005d     Document Type: Article

References (27)

1. For recent reviews on diastereoselection, see a thematic issue: (a) le Noble, W. J.; Gung, B. W. Chem. Rev. 1999, 99, 1069-1480.
2. (b) Mehta, G.; Chandrasekhar, J. Chem. Rev. 1999, 99, 1437.
3. (c) Li, H.; le Noble, W. J. Recl. Trav. Chim. Pays-Bas 1992, 111, 199.
4. (a) Mehta, G.; Khan, F. A. J. Am. Chem. Soc. 1990, 112, 6140.
5. (b) Mehta G.; Khan, F. A. J. Chem. Soc., Chem. Commun. 1991, 18.
6. (c) Ganguly B.; Chandrasekhar, J.; Khan, F. A.; Mehta, G. J. Org. Chem. 1993, 58, 1734.
7. (d) Mehta, G.; Khan, F. A.; Gadre, S. R.; Shirsat, R. N.; Ganguly, B.; Chandrasekhar, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1390.
8. (e) Mehta, G.; Khan, F. A.; Ganguly, B.; Chandrasekhar, J. J. Chem. Soc., Chem. Commun. 1992, 1711.
9. (f) Tsuji, M.; Ohwada, T.; Shudo, K. Tetrahedron Lett. 1997, 38, 6693.
10. (g) Mehta, G.; Ravikrishna, C.; Ganguly, B.; Chandrasekhar, J. J. Chem. Soc., Chem. Commun. 1997, 75.
11. (h) Mehta, G.; Ravikrishna, C.; Gadre, S. R.; Suresh, C. H.; Kalyanraman, P.; Chandrasekhar, J. Chem. Commun. 1998, 975.
12. Mehta, G.; Singh, R. S.; Gagliardini, V.; Deva Priyakumar, P.; Sastry, G. N. Tetrahedron Lett. 2001, 42, 8527.
13. Conti, P.; Kozikowski, A. P. Tetrahedron Lett. 2000, 41, 4053.
14. 13C NMR, and MS) data. Experimental details and characterization data are provided in Supporting Information.
15. Cieplak, A. S. J. Am. Chem. Soc. 1981, 103, 4540.
16. (a) Paddon-Row, M. N.; Wu, Y.-D.; Houk, K. N. J. Am. Chem. Soc. 1992, 114, 10638.
17. (b) Broughton, H. B.; Green, S. M.; Rzepa, H. S. J. Chem. Soc., Chem. Commun. 1992, 998.
18. A}, and ρ(r) denotes the molecular electron density. The critical points (CP) of the function are defined as the points at which ∇V(r) = 0 and the minima are characterized as (3, +3). Lone pairs, π-bonds, etc. appear as negative-valued minima in MESP.
19. (a) Atoms in Molecules: A Quantum Theory, Bader, R. F. W., Ed.; Oxford University Press: Oxford, 1990.
20. (b) Shirsat, R. N.; Bapat, S. V.; Gadre, S. R. Chem. Phys. Lett. 1992, 200, 373.
21. (c) Gadre, S. R. In Computational Chemistry: Reviews in Current Trends; Leszczynski, Jerzy, Ed.; World Scientific: Singapore, 1999; Vol. 4, pp 1-53.
22. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, revision E.2; Gaussian, Inc.: Pittsburgh, PA, 1995.
23. UNIPROP, Molecular Property Calculation Package; Theoretical Chemistry Group, Department of Chemistry, University of Pune: Pune, India, April 1993.
24. UNIVIS-2000: An Indigenously Developed Visualization Package Limaye, A. C.; Gadre, S. R. Curr. Sci. (India) 2001, 80, 1296.
25. (a) Gadre, S. R.; Pundlik, S. S. J. Phys. Chem. 1997, B101, 9657.
26. (b) Gadre, S. R.; Bhadane, P. K.; Pundlik, S. S.; Pingale, S. S. In Molecular Electrostatic Potential: Concepts and Applications; Murray, J., Sen, K. D., Eds.; Elsevier: 1996; Chapter 5, p 219.
27. Breneman, C. M.; Wilberg, K. B. J. Comput. Chem. 1990, 11, 361.