Highly stereoselective ring expansion of enantiopure α-hydroxyalkyl azetidines |
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Authors: | Franç ois CoutyFranç ois Durrat,Damien Prim |
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Affiliation: | Laboratoire SIRCOB, UMR CNRS 8086, Bâtiment Lavoisier, Université de Versailles, 45, avenue des Etats-Unis, F-78035 Versailles Cedex, France |
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Abstract: | Stereodefined α-hydroxyalkyl azetidines, prepared in a few steps from enantiopure β-amino alcohols, are chlorinated or transformed into methanesulfonyloxymethyl derivatives in good yields. Heating of these compounds in chloroform or dimethylformamide induces a stereospecific ring enlargement to give 3-chloro or 3-methanesulfonyloxy pyrrolidines. The ease of this rearrangement depends on the nature of the migrating group (Cl− or MsO−), of the class of the starting alcohol (primary or secondary) and of the relative stereochemistry of the starting material. |
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