A Practical Synthesis of Azetidine

Allenylidene Ligand of [Ru(η5-C5H5)(CCCPh2)(CO)(PPri3)]BF4 as Entry to Novel Unsaturated η1-Carbon Ligands Containing Azetidine and Hexahydroquinoline Skeletons

“…Accordingly, several alternative methods have been used. Azetidines can be prepared via the direct alkylation of benzhydrylamine with 1-bromo-3-chloropropane and subsequent hydrogenolysis . 2-Methyleneazetidines have been synthesized in high yield via closure of N -aryl β-chloro ketimines induced by potassium tert -butoxide .…”

Lithiation–Electrophilic Substitution of N‐Thiopivaloylazetidine

“…[3] Herein, we report a promising route to 2substituted azetidines from azetidine itself, the latter being readily available in multi-kilogram quantities. [4] There are few previous studies concerning the reaction of the a-CÀH bonds of N-substituted azetidine. The two-step introduction of some nucleophiles at the C2-position of Ntosylazetidine (1, PG = Ts) has been achieved using anodic C2 acetoxylation, [5] whilst the attempted direct CÀH insertion of N-Boc-azetidine (1, PG= Boc) using methyl phenyldiazoacetate under Rh II catalysis formed a complex mixture of products (normal-sized azacycles were much more effective).…”

Lithiation–Electrophilic Substitution of N‐Thiopivaloylazetidine

“…Substituted azetidines are often challenging to synthesize but have significance and current interest as bioactive entities; they have also been used as ligands in metal‐catalyzed transformations and as chiral auxiliaries 3. Herein, we report a promising route to 2‐substituted azetidines from azetidine itself, the latter being readily available in multi‐kilogram quantities 4…”