Ouverture sélective d'époxydes styréniques substitués à l'aide d'azoture de lithium en présence de β-cyclodextrine | Zendy

Alain Guy | Zendy; Joël Doussot | Zendy; Agnès Dallamaggiore | Zendy; Robert Garreau | Zendy

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Ouverture sélective d'époxydes styréniques substitués à l'aide d'azoture de lithium en présence de β-cyclodextrine

Author(s) -

Alain Guy,

Joël Doussot,

Agnès Dallamaggiore,

Robert Garreau

Publication year - 1995

Publication title -

canadian journal of chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.323

H-Index - 68

eISSN - 1480-3291

pISSN - 0008-4042

DOI - 10.1139/v95-077

Subject(s) - chemistry , regioselectivity , epoxide , kinetic resolution , cyclodextrin , enantioselective synthesis , stereochemistry , lithium (medication) , medicinal chemistry , organic chemistry , catalysis , medicine , endocrinology

Regio- and enantioselective opening of substituted styrenic epoxides by lithium azide in presence of β-cyclodextrin is described. The regioselectivity of the reaction is related to the hydrophobicity of the substrate, which governs its penetration inside the cavity of the cyclodextrin and is favorable to the β opening of the epoxide. The enantioselectivity observed during the kinetic resolution of the racemic epoxide is mainly dependent on the non-covalent interactions between the upper rim of the cyclodextrin and the epoxide. Keywords: β-cyclodextrin, inclusion complexes, regio- and stereocontrol, chemistry in aqueous medium.

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