Intramolecular 4 + 3 cycloadditions. A theoretical analysis of simple diastereoselectivity in reactions of alkoxyallylic cations and furans

Organic Letters

Volumn 3, Issue 23, 2001, Pages 3663-3665

  Harmata, Michael ^c   Schreiner, Peter R ^a,b  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

^b UNIVERSITY OF GEORGIA   (United States)

^c UNIVERSITY OF MISSOURI   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0041905294     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016611t     Document Type: Article

References (17)

1. For reviews on 4 + 3 cycloaddition chemistry, see: (a) Rigby, J. H.; Pigge, F. C. [4 + 3] Cycloaddition reactions. Org. React. 1997, 51, 351-478.
2. (b) Harmata, M. Intramolecular [4 + 3] cycloaddition reactions. Adv. Cycloaddit. 1997, 4, 41-86.
3. (c) Harmata, M. Heteroatom-stabilized allylic cations in 4 + 3 cycloaddition reactions. Recent Res. Dev. Org. Chem. 1997, 1, 523-535.
4. (d) Harmata, M. Intramolecular cycloaddition reactions of allylic cations. Tetrahedron 1997, 53, 6235-6280.
5. (d) Cha, J. K.; Oh, J. [4 + 3] cycloaddition reactions of cyclic oxyallyls in natural product synthesis. Curr. Org. Chem. 1998, 2, 217-232.
6. Harmata, M. Acc. Chem. Res. 2001, 34, 595-605.
7. For other theoretical treatments of the 4 + 3 cycloaddition reaction, see: (a) Cramer, C. J.; Harmata, M.; Rashatasakhon, P. J. Org. Chem. 2001, 66, 5641-5644.
8. (b) Cramer, C. J.; Barrows, S. E. J. Org. Chem. 1998, 63, 5523-5532.
9. Cramer, C. J.; Barrows, S. E. J. Phys. Org. Chem. 2000, 13, 176-186.
10. Harmata, M.; Gamlath, C. B. J. Org. Chem. 1989, 53, 6154-6156.
11. Harmata, M.; Gamlath, C. B.; Barnes, C. L. Tetrahedron Lett. 1990, 31, 5981-5984.
12. (a) Harmata, M.; Gamlath, C. B.; Barnes, C. L. Tetrahedron Lett. 1993, 34, 265-268.
13. (b) Harmata, M.; Gamlath, C. B.; Barnes, C. L.; Jones, D. E. J. Org. Chem. 1995, 60, 5077-5092.
14. Gaussian 98. A9. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; J. A. Montgomery, J.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; J. M. Millam; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian, Inc.: Pittsburgh, PA, 1999.
15. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5662.
16. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
17. (b) Miehlich, B.; Savin, A.; Stoll, H.; Preuss, H. Chem. Phys. Lett. 1989, 157, 200-216.