Electroreductive intramolecular coupling of aromatic imino esters: Is four-membered cyclization much more favorable than six-membered cyclization?

Organic Letters

Volumn 8, Issue 7, 2006, Pages 1323-1325

  Kise, Naoki ^a   Hirano, Yuuki ^a   Tanaka, Yoshi ^a  

^a TOTTORI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRROLIDONE DERIVATIVE; ASPARTIC ACID; AZETIDINE DERIVATIVE; ESTER; GLUTAMIC ACID; IMINE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

ASPARTIC ACID; AZETIDINES; CYCLIZATION; ESTERS; GLUTAMIC ACID; IMINES; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PYRROLIDINONES; STEREOISOMERISM;

EID: 33645939222     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol053144x     Document Type: Article

References (12)

1. Kise, N.; Ozaki, H.; Moriyama, N.; Kitagishi, Y.; Ueda, N. J. Am. Chem. Soc. 2003, 125, 11591-11596.
2. Kise, N.; Ohya, K.; Arimoto, K.; Yamashita, Y.; Hirano, Y.; Ono, T.; Ueda, N. J. Org. Chem. 2004, 69, 7710-7719.
3. For recent reviews, see the following, (a) Formation of four-membered heterocycles through electrophilic heteroatom cyclization: Robin, S.; Rousseau, G. Eur. J. Org. Chem. 2002, 3099-3114.
4. (b) Formation of four-membered carbocycles: Hartley, R. C.; Caldwell, S. T. Perkin 1 2000, 477-501.
5. For recent reports for the asymmetric synthesis of multisubstituted azetidines, see: (a) Burtoloso, A. C. B.; Correia, C. R. D. J. Organomet. Chem. 2005, 690, 5636.
6. (b) De Talancé, V. L.; Banide, E.; Bertin, B.; Comesse, S.; Kadouri-Puchot, C. Tetrahedron Lett. 2005, 46, 8023.
7. (c) Bräuner-Osborne, H.; Bunch, L.; Chopin, N.; Couty, F.; Evano, G.; Jensen, A. A.; Kusk, M.; Nielsen, B.; Rabasso, N. Org. Biomol. Chem. 2005, 3, 3926.
8. (d) Mendler, B.; Kazmaier, U.; Huch, V.; Veith, M. Org. Lett. 2005, 7, 2643.
9. (e) Couty, F.; Evano, G.; Vargas-Sanchez, M.; Bouzas, G. J. Org. Chem. 2005, 70, 9028.
10. 1 a complex mixture was formed in the absence of CTMS.
11. The calculations were carried out using the Gaussian 03W program: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; 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.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03. revision B.02; Gaussian, Inc.: Pittsburgh, PA, 2003.
12. It was confirmed that the optimized structures had only one imaginary frequency according to the vibration analysis. The imaginary frequency was verified to be consistent with the intramolecular coupling by displaying the vibrational mode using the Gauss View program.