The aldol-type addition of enol borinates to imines was studied with ab initio MO methods (3-21G basis set). Calculations performed on unsubstituted, mono- and di-substituted structures have shown that only two competing cyclic transition states (chair-like and boat-like) are important. Their relative energy depends on the enolate geometry and on the substitution pattern. This approach allows a qualitative rationalization of the observed stereoselectivity trends in the title reaction. (C) 1997 Elsevier Science Ltd.

Computational studies on the aldol-type addition of boron enolates to imines: An ab-initio approach / A. Bernardi, C.M.A. Gennari, L. Raimondi, M. Villa. - In: TETRAHEDRON. - ISSN 0040-4020. - 53:22(1997), pp. 7705-7714.

Computational studies on the aldol-type addition of boron enolates to imines: An ab-initio approach

A. Bernardi
Primo
;
C.M.A. Gennari
Secondo
;
L. Raimondi
Penultimo
;
1997

Abstract

The aldol-type addition of enol borinates to imines was studied with ab initio MO methods (3-21G basis set). Calculations performed on unsubstituted, mono- and di-substituted structures have shown that only two competing cyclic transition states (chair-like and boat-like) are important. Their relative energy depends on the enolate geometry and on the substitution pattern. This approach allows a qualitative rationalization of the observed stereoselectivity trends in the title reaction. (C) 1997 Elsevier Science Ltd.
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/175956
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