Tetrahedron p. 537 - 540 (1985)
Update date:2022-08-04
Topics:
Agami, Claude
Rizk, Toufic
Kinetically controlled oxazolidine formation was observed with aromatic aldehydes substituted by electron-withdrawing groups.The stereoselectivity is solvent dependent: non-stereoselective ring closure occurred in chloroform while a high diastereodifferentiation was observed in methanol.The first oxazolidine showing an unambiguous 2R configuration was synthesized from p-bromobenzaldehyde and (-)-ephedrine in alcohol medium.A mechanism involving a nucleophilic assistance by alcoholic solvents is suggested in order to clarify the differences in stereoselectivity.
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