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Preparation of Enantiomerically Pure 4-Alkyl-5-formyl-4-nitrocyclohex-1-enes from 5-Glyco-4-nitrocyclohex-1-enes by R. Ballini; G. Bosica; M.V. Gil; E. Román; J.A. Serrano is a Chemistry article available to read on EtoBox.

What is Preparation of Enantiomerically Pure 4-Alkyl-5-formyl-4-nitrocyclohex-1-enes from 5-Glyco-4-nitrocyclohex-1-enes about?

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 a,b-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 (NaIO 4 ). 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.

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Author

R. Ballini; G. Bosica; M.V. Gil; E. Román; J.A. Serrano

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0957-4166)

Published

2002

Language

EN

Field

Chemistry (Physical Sciences)