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Title: | Preparation of enantiomerically pure 4-alkyl-5-formyl-4-nitrocyclohex-1-enes from 5-glyco-4-nitrocyclohex-1-enes |
Authors: | Ballini, Roberto Bosica, Giovanna Gil, Maria Victoria Roman-Galan, Emilio Serrano, Jose A. |
Keywords: | Chemical reactions Chemistry, Analytic Catalysts -- Analysis |
Issue Date: | 2002 |
Publisher: | Pergamon Press |
Citation: | Ballini, R., Bosica, G., Gil, M. V., Roman-Galan, E., & Serrano, Jose A. (2002). Preparation of enantiomerically pure 4-alkyl-5-formyl-4-nitrocyclohex-1-enes from 5-glyco-4-nitrocyclohex-1-enes. Tetrahedron: Asymmetry, 13(16), 1773-1787. |
Abstract: | Base-catalyzed (TMG, DBU or TEA) asymmetric Michael reactions between 5-glyco-4-nitrocyclohex-1-enes 1a or 1b and a number of mono- or α,β-disubstituted electron-deficient alkenes yielded, in all cases, adducts in which the sugar side-chain and the added group on C-4 of the cyclohexene ring showed a trans-relationship. Furthermore, some of the adducts have been used to prepare enantiomerically pure 4-alkyl-5-formyl-4-nitrocyclohex-1-enes by a two-step process involving base-catalyzed (NaOMe) deacetylation of their respective sugar side-chains and subsequent oxidative cleavage (NaIO4). When reactions of 1a or 1b with dimethyl maleate, dimethyl fumarate or methyl trans-4-oxopentenoate were carried out with DBU (instead of TMG) as catalyst, there was in situ elimination of nitrous acid. |
URI: | https://www.um.edu.mt/library/oar//handle/123456789/24872 |
Appears in Collections: | Scholarly Works - FacSciChe |
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