A study on the open chain model for transition state structures in the nucleophilic addition to β-substituted carbonyl compounds and its application to the 1,3 asymmetric induction

Tetrahedron

Volumn 53, Issue 39, 1997, Pages 13419-13426

  Bonini, Carlo ^a   Esposito, Vittorio ^a   D'Auria, Maurizio ^a   Righi, Giuliana ^b  

^a UNIVERSITY OF BASILICATA   (Italy)

^b SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; DIPOLE; ENERGY; MODEL; PRIORITY JOURNAL; QUANTUM MECHANICS; REACTION ANALYSIS;

EID: 0030851176     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00853-3     Document Type: Article

References (22)

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12. (e) Nakada, M.; Urano, J.; Kobayashi, S.; Ohno, M. Tetrahedron Lett. 1994, 35, 741-744.
13. (f) Evans, D. A.; Duffy, J. L.; Dart, M. J. Tetrahedron Lett. 1994, 35, 8537-8540.
14. (g) Evans, D. A.; Dart, M. J.; Duffy, J. L.; Yang, M. G. J. Am. Chem. Soc. 1996, 118, 4322-4343.
15. (h) Evans, D. A.; Duffy, J. L.; Dart, M J. Tetrahedron Lett. 1994, 35, 8541-8544.
16. 5g, and the kinetic control of the reaction imply that the nature of the nucleophiles should not be decisive for the trend of the diastereoselectivity.
17. 5g and our data are in good agreement with those published.
18. MM+ Force Field was used for molecular mechanics and Polak-Ribiere algorithm with gradient calculations was adopted for geometry optimization. Semi-empirical electronic total energy estimate and refinement of the geometry were performed with AM1 or PM3 parameter set, depending on the availability of parameters for metal atoms.
19. 1 for entry 3, appears mainly depending from the bulky phenyl substituents.
20. 5h on his proposed model for diastereoselective reduction of β-alkoxy ketones.
21. Ukaji, Y.; Kanda, K.; Yamamoto, K.; Fujisawa, T. Chem. Lett., 1990, 597-600.
22. It has been found that more sterically demanding hydride donors, in the reduction of β-susbtituted ketones, have improved the diastereoselective ratio .