Title of article
Studies on diastereoselective reduction of cyclic β-ketoesters with boron hydrides. Part 4: The reductive profile of functionalized cyclohexanone derivatives
Author/Authors
Carlos A.M. Fraga، نويسنده , , Lis Helena P Teixeira، نويسنده , , Carla Maria de S Menezes، نويسنده , , Carlos Mauricio R SantʹAnna، نويسنده , , Maria da Conceiç?o K.V Ramos، نويسنده , , Francisco Radler de Aquino Neto، نويسنده , , Eliezer J. Barreiro، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2004
Pages
11
From page
2745
To page
2755
Abstract
Reduction of 2-allyl-2-carboalkoxycyclohexanones (), 2-propyl-2-carboethoxycyclohexanone () and 2-benzyl-2-carboethoxycyclohexanone () with boron hydrides in the presence and absence of several chelating agents were studied. Molecular modeling studies using semiempirical PM3 method were performed in order to find a suitable explanation of the diastereoselection of ketone carbonyl faces during the reductive process, which yielded trans-2-allyl-2-carboethoxycyclohexanol () and cis-2-allyl-2-carboethoxycyclohexanol () in good diastereomeric excess by using inexpensive sodium and tetrabutylammonium borohydrides.
Keywords
Boron hydrides , Ketoesters , Diastereoselective reduction
Journal title
Tetrahedron
Serial Year
2004
Journal title
Tetrahedron
Record number
1085135
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