Optically active heterocyclic allyl sulphides 1.7 react with organomagnesium compounds in the presence of CuBr to afford optically active alkenes in good yields and very high T-selectivity. The regioselectivity depends on the solvent as well on the CuBr: allylic sulphide ratio. The heterocyclic nucleus imparts asymmetric induction in the range of 50-98% ee. The regio- and enantio-selectivity of these reactions would be related to the coordination exerted by the heterocyclic nitrogen toward the copper organyi.
Copper-mediated Regio- and Enantio-selective Cross-coupling of Heterocyclic Allyl Sulphides with Organomagnesium Compounds: A Case of 1,7-Relative Stereogenesis
NACCI, Angelo;
1996-01-01
Abstract
Optically active heterocyclic allyl sulphides 1.7 react with organomagnesium compounds in the presence of CuBr to afford optically active alkenes in good yields and very high T-selectivity. The regioselectivity depends on the solvent as well on the CuBr: allylic sulphide ratio. The heterocyclic nucleus imparts asymmetric induction in the range of 50-98% ee. The regio- and enantio-selectivity of these reactions would be related to the coordination exerted by the heterocyclic nitrogen toward the copper organyi.File in questo prodotto:
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