A sulfinyl-directed asymmetric [5C + 2C] intramolecular acetoxypyranone-alkene cycloaddition

Organic Letters

Volumn 4, Issue 21, 2002, Pages 3683-3685

  López, Fernando ^a   Castedo, Luis ^a   Mascareñas, José L ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

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ARTICLE;

EID: 0346551904     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026633v     Document Type: Article

References (16)

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6. Intermolecular 3-oxidopyridinium-vinylsulfoxide cycloadditions have been previously reported, but they exhibit modest yields and relatively poor stereoselectivities: (a) Takahashi, T.; Kitano, K.; Hagi, T.; Nihonmatsu, H.; Koizumi, T. Chem. Lett. 1989, 597.
7. (b) Araldi, G. L.; Prakash, K. R. C.; George, C.; Kozikowski, A. P. Chem. Commun. 1997, 1875.
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13. 3 using a racemic mixture as a reference.
14. Domingo, L. C.; Zaragoza, R. J. J. Org. Chem. 2000, 65, 5480.
15. Calculations were performed using the Gaussian 98 set of programs. Geometries were preoptimized by the semiempirical PM3 method. Stationary points were optimized at the B3LYP/6-31G* level of theory. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; 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. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, version A-7; Gaussian, Inc.: Pittsburgh, PA, 1998.
16. Calculated C=C-S-O dihedral angle for s-cis: 9°. Calculated C=C-S-O dihedral angle for s-trans: 127°. This last conformer is 0.81 kcal/mol less stable than s-cis. For previous conformational studies of α,β-unsaturated sulfoxides, see: Tietze, L. F.; Schffenhauer, A.; Schreiner, P. R. J. Am. Chem. Soc. 1998, 120, 7952.