Computational studies on the asymmetric induction in intramolecular 1,3- dipolar cycloaddition of (S)-5-phenyl-morpholin-2-one

Tetrahedron Letters

Volumn 41, Issue 26, 2000, Pages 5077-5081

  Drew, Michael G B ^a   Harwood, Laurence M ^a   Price, David W ^a   Choi, M S ^b   Park, Gyoosoon ^b  

^a UNIVERSITY OF READING   (United Kingdom)

^b Kookmin University   (South Korea)

Author keywords

1,3 dipolar cycloaddition; Ab initio; Activation barrier; Semi empirical; Transition state

Indexed keywords

5 PHENYL MORPHOLIN 2 DERIVATIVE; MORPHOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; DIASTEREOISOMER; ENANTIOMER; GEOMETRY; MATHEMATICAL MODEL; QUANTUM MECHANICS; STEREOSPECIFICITY;

EID: 0034709654     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00777-2     Document Type: Article

References (16)

1. Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon, 1990.
2. Harwood, L. M.; Lilley, I. A. Tetrahedron: Asymmetry 1995, 6, 1557; Anslow, A. S.; Cox, G. G.; Harwood, L. M.; Chemistry of Heterocyclic Compounds 1995, 10, 1393; Anslow, A. S.; Harwood, L. M.; Lilley, I. A. Tetrahedron: Asymmetry 1995, 6, 2465; Alker, D.; Harwood, L. M.; Williams, C. E. Tetrahedron 1997, 53, 12671; Alker, D.; Harwood, L. M.; Williams, C. E. Tetrahedron Lett. 1998, 39, 475; Alker, D.; Hamblett, G.; Harwood, L. M.; Robertson, S. M.; Watkin, D. J.; Williams, C. E. Tetrahedron 1998, 54, 6089; Harwood, L. M.; Robertson, S. M. J. Chem. Soc., Chem. Commun. 1998, 2641.
3. Harwood, L. M.; Lilley, I. A. Tetrahedron: Asymmetry 1995, 6, 1557; Anslow, A. S.; Cox, G. G.; Harwood, L. M.; Chemistry of Heterocyclic Compounds 1995, 10, 1393; Anslow, A. S.; Harwood, L. M.; Lilley, I. A. Tetrahedron: Asymmetry 1995, 6, 2465; Alker, D.; Harwood, L. M.; Williams, C. E. Tetrahedron 1997, 53, 12671; Alker, D.; Harwood, L. M.; Williams, C. E. Tetrahedron Lett. 1998, 39, 475; Alker, D.; Hamblett, G.; Harwood, L. M.; Robertson, S. M.; Watkin, D. J.; Williams, C. E. Tetrahedron 1998, 54, 6089; Harwood, L. M.; Robertson, S. M. J. Chem. Soc., Chem. Commun. 1998, 2641.
4. Harwood, L. M.; Lilley, I. A. Tetrahedron: Asymmetry 1995, 6, 1557; Anslow, A. S.; Cox, G. G.; Harwood, L. M.; Chemistry of Heterocyclic Compounds 1995, 10, 1393; Anslow, A. S.; Harwood, L. M.; Lilley, I. A. Tetrahedron: Asymmetry 1995, 6, 2465; Alker, D.; Harwood, L. M.; Williams, C. E. Tetrahedron 1997, 53, 12671; Alker, D.; Harwood, L. M.; Williams, C. E. Tetrahedron Lett. 1998, 39, 475; Alker, D.; Hamblett, G.; Harwood, L. M.; Robertson, S. M.; Watkin, D. J.; Williams, C. E. Tetrahedron 1998, 54, 6089; Harwood, L. M.; Robertson, S. M. J. Chem. Soc., Chem. Commun. 1998, 2641.
5. Harwood, L. M.; Lilley, I. A. Tetrahedron: Asymmetry 1995, 6, 1557; Anslow, A. S.; Cox, G. G.; Harwood, L. M.; Chemistry of Heterocyclic Compounds 1995, 10, 1393; Anslow, A. S.; Harwood, L. M.; Lilley, I. A. Tetrahedron: Asymmetry 1995, 6, 2465; Alker, D.; Harwood, L. M.; Williams, C. E. Tetrahedron 1997, 53, 12671; Alker, D.; Harwood, L. M.; Williams, C. E. Tetrahedron Lett. 1998, 39, 475; Alker, D.; Hamblett, G.; Harwood, L. M.; Robertson, S. M.; Watkin, D. J.; Williams, C. E. Tetrahedron 1998, 54, 6089; Harwood, L. M.; Robertson, S. M. J. Chem. Soc., Chem. Commun. 1998, 2641.
6. Harwood, L. M.; Lilley, I. A. Tetrahedron: Asymmetry 1995, 6, 1557; Anslow, A. S.; Cox, G. G.; Harwood, L. M.; Chemistry of Heterocyclic Compounds 1995, 10, 1393; Anslow, A. S.; Harwood, L. M.; Lilley, I. A. Tetrahedron: Asymmetry 1995, 6, 2465; Alker, D.; Harwood, L. M.; Williams, C. E. Tetrahedron 1997, 53, 12671; Alker, D.; Harwood, L. M.; Williams, C. E. Tetrahedron Lett. 1998, 39, 475; Alker, D.; Hamblett, G.; Harwood, L. M.; Robertson, S. M.; Watkin, D. J.; Williams, C. E. Tetrahedron 1998, 54, 6089; Harwood, L. M.; Robertson, S. M. J. Chem. Soc., Chem. Commun. 1998, 2641.
7. Harwood, L. M.; Lilley, I. A. Tetrahedron: Asymmetry 1995, 6, 1557; Anslow, A. S.; Cox, G. G.; Harwood, L. M.; Chemistry of Heterocyclic Compounds 1995, 10, 1393; Anslow, A. S.; Harwood, L. M.; Lilley, I. A. Tetrahedron: Asymmetry 1995, 6, 2465; Alker, D.; Harwood, L. M.; Williams, C. E. Tetrahedron 1997, 53, 12671; Alker, D.; Harwood, L. M.; Williams, C. E. Tetrahedron Lett. 1998, 39, 475; Alker, D.; Hamblett, G.; Harwood, L. M.; Robertson, S. M.; Watkin, D. J.; Williams, C. E. Tetrahedron 1998, 54, 6089; Harwood, L. M.; Robertson, S. M. J. Chem. Soc., Chem. Commun. 1998, 2641.
8. Harwood, L. M.; Lilley, I. A. Tetrahedron: Asymmetry 1995, 6, 1557; Anslow, A. S.; Cox, G. G.; Harwood, L. M.; Chemistry of Heterocyclic Compounds 1995, 10, 1393; Anslow, A. S.; Harwood, L. M.; Lilley, I. A. Tetrahedron: Asymmetry 1995, 6, 2465; Alker, D.; Harwood, L. M.; Williams, C. E. Tetrahedron 1997, 53, 12671; Alker, D.; Harwood, L. M.; Williams, C. E. Tetrahedron Lett. 1998, 39, 475; Alker, D.; Hamblett, G.; Harwood, L. M.; Robertson, S. M.; Watkin, D. J.; Williams, C. E. Tetrahedron 1998, 54, 6089; Harwood, L. M.; Robertson, S. M. J. Chem. Soc., Chem. Commun. 1998, 2641.
9. (a) Harwood, L. M.; Lilley, I. A. Tetrahedron Lett. 1993, 34, 537.
10. (b) Harwood, L. M.; Kitchen, L. C. Tetrahedron Lett. 1993, 34, 6603.
11. (c) Harwood, L. M.; Lilley, I. A. Synlett 1996, 1010.
12. CS Chem3D 5.0, CambridgeSoft Corporation.
13. Gaussian-94, Revision E.1., 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, Inc., Pittsburgh, PA, 1995.
14. Conformational analysis of 5-phenyl-N-methylene-morpholin-2-one shows two low energy conformations containing a half-chair ylide with the 5-phenyl group positioned either in an equatorial or a pseudo-axial position, the former, which is used in the present calculations, is predicted to be the more stable conformer by 0.23 kcal/mol.
15. Calculated energies at HF/3-21G are -816.4505277 hartree for eTEa′ and -816.2420800 hartree for yTZs′.
16. For a recent theoretical study of the rotational barrier in ylides, see: Yoshioka, Y.; Yamaki, D.; Kiribayashi, S.; Tsunesada, T.; Nishino, M.; Yamaguchi, K.; Mizuno, K.; Satto, I. Electron. J. Theor. Chem. 1997, 2, 218.