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Volumn 14, Issue 19, 2008, Pages 5851-5860

Pyridine-catalyzed stereoselective addition of acyclic 1,2-diones to acetylenic esters: Synthetic and theoretical studies of an unprecedented rearrangement

Author keywords

Benzoyl migration; Density functional calculations; Diaroyl maleates; Pyridine catalysis; Reaction mechanisms

Indexed keywords

ACETYLENE; CARBOXYLATION; CATALYSIS; DENSITY FUNCTIONAL THEORY; ESTERIFICATION; ESTERS; ISOMERS; LIGHTING; NETWORK PROTOCOLS; ORGANIC COMPOUNDS; ORGANIC POLYMERS; PROBABILITY DENSITY FUNCTION; STEREOCHEMISTRY; STEREOSELECTIVITY;

EID: 53849093042     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200800250     Document Type: Article
Times cited : (23)

References (56)
  • 14
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    • [1,3] which show that the zwitterion 1 adds to another molecule of acetylenic ester to form a second zwitterion, which then cyclizes to form 4H-quinolizine. Evidently the addition product from a transoid zwitterion would not undergo such a cyclization.
    • [1,3] which show that the zwitterion 1 adds to another molecule of acetylenic ester to form a second zwitterion, which then cyclizes to form 4H-quinolizine. Evidently the addition product from a transoid zwitterion would not undergo such a cyclization.
  • 28
    • 53849147631 scopus 로고    scopus 로고
    • Gaussian 03, Revision C.02, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr, T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayak
    • Gaussian 03, Revision C.02, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian, Inc.: Wallingford CT, 2004.
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    • We have also optimised the structures of transition states TS1 and TS2 by using the basis set 6-31+G(d,p) consisting of the polarisation and diffused functions at the B3LYP level. These structures were very similar to the B3LYP/6-31G(d) level structures and the activation free energy values were nearly unchanged. Further, the TS1 geometry showed only minor structural changes when optimised with PCM at the B3LYP/6-301G(d) level. See the Supporting Information for more details
    • We have also optimised the structures of transition states TS1 and TS2 by using the basis set 6-31+G(d,p) consisting of the polarisation and diffused functions at the B3LYP level. These structures were very similar to the B3LYP/6-31G(d) level structures and the activation free energy values were nearly unchanged. Further, the TS1 geometry showed only minor structural changes when optimised with PCM at the B3LYP/6-301G(d) level. See the Supporting Information for more details.


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