The origin of the stereoselectivity in the asymmetric Michael reaction using chiral imines/secondary enamines under neutral conditions: A computational investigation

Tetrahedron Asymmetry

Volumn 9, Issue 6, 1998, Pages 1059-1064

  Tran Huu Dau, Marie E ^a   Riche, Claude ^a   Dumas, Françoise ^a   D'Angelo, Jean ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID METHYL ESTER; ALPHA METHYLBENZYLAMINE; ENAMINE; IMINE; KETONE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; CYCLIZATION; ENTHALPY; MOLECULAR INTERACTION; PRIORITY JOURNAL; PROTON TRANSPORT; STEREOCHEMISTRY;

EID: 0001673924     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00063-9     Document Type: Article

References (17)

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2. Reviews: (a) d'Angelo, J.; Desmaële, D.; Dumas, F.; Guingant, A. Tetrahedron: Asymmetry 1992, 3, 459-505. (b) d'Angelo, J.; Cavé, C.; Desmaële, D.; Dumas, F. Trends in Organic Chemistry, Pandalai, S. G., Ed.; Trivandrum: India, 1993, Vol 4, pp 555-615.
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16. For 7d, the potential barrier of rotation around the C7-C9 bond has been evaluated. In the preferred conformation, the phenyl plane is eclipsing the C7-H bond. The torsion angle N6-C7-C9-C10 is -121.3°, while in the crystal structure, the corresponding angle is -138.5°. While for 7d and 7e, only one degree of freedom allows us to describe the conformational space, for 7g, we must take into account the rotation around the single bond C7-C9. See also: Haviari, G.; Célérier, J.-P.; Petit, H.; Lhommet, G.; Gardette, D.; Gramain, J.-C. Tetrahedron Lett. 1992, 33, 4311-4312.
17. 3