Tetrahedron Letters p. 5209 - 5212 (2003)
Update date:2022-08-05
Topics:
Couty, Fran?ois
Durrat, Fran?ois
Prim, Damien
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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