A General and Scalable Method toward Enantioenriched C2-Substituted Azetidines Using Chiral <i>tert</i>-Butanesulfinamides.

ABSTRACT: Diverse ranges of chiral nitrogen-containing heterocycles serve as a molecular toolbox for modulating a wide array of biological processes, but enantioenriched production of smaller chiral heterocycles is a bottleneck. There is a lack of general approaches for the stereoselective preparation of chiral 4-membered monocyclic C2-substituted azetidines, where many routes to different substitution types are possible, but no simple and common approach exists. To bridge this gap, inexpensive and widely available chiral tert-butanesulfinamides are harnessed for chiral induction with 1,3-bis-electrophilic 3-chloropropanal, providing a three-step approach to C2-substituted azetidines with aryl, vinyl, allyl, branched alkyl, and linear alkyl substituents. Eleven azetidine products are produced

SUBMITTER: Zelch D 

PROVIDER: S-EPMC11494643 | biostudies-literature | 2024 Oct

REPOSITORIES: biostudies-literature