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40.1.6 Product Subclass 6: Azetidines

DOI: 10.1055/sos-SD-040-00515

Couty, F.Science of Synthesis, (200940773.

General Introduction

Compared to their lower homologues (aziridines) and their higher homologues (pyrrolidines and piperidines), azetidines belong to a less studied class of cyclic amines. However, within the past decades, a clear renewal of interest for this class of heterocycle has appeared and this has been solidified by the publication of many new methods for their synthesis, especially for the preparation of nonracemic derivatives. Azetidines are therefore finding growing applications in the field of medicinal chemistry and as new chiral ligands or organocatalysts for enantioselective transformations. Azetidine syntheses have been regularly reviewed: up to 1964 by Moore,[‌1‌] up to 1979 by Cromwell,[‌2‌] up to 1983 by Moore,[‌3‌] and up to 1995 by De Kimpe;[‌4‌] see also HoubenWeyl, Vol. E 16c, p 729. More specialized reviews in the field of azetidines have been published, including a review on the chemistry of azetidin-3-ones,[‌5‌] the syntheses of enantiomerically pure azetidines,[‌6‌] the syntheses of azetidine-2-carboxylic acid and derivatives,[‌7‌] and a review on ring-expansion and ring-opening processes starting from this heterocycle.[‌8‌]

References


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