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40.1.6.2.1.3.5 Ring Closure of β,γ-Epoxyamines

DOI: 10.1055/sos-SD-140-00195

Couty, F.Science of Synthesis Knowledge Updates, (20172456.

Ring closure of β,γ-epoxyamines leading to an azetidin-3-ol through a 4-endo-tet ring closure is anecdotal, but in the course of a work on the optimized large-scale (kg) synthesis of 1-benzhydrylazetidin-3-ol (23; Scheme 5), it was demonstrated through independent experiments that minor quantities (2–4%) of amino epoxide 22, produced during the ring closure of γ-chloroamine 21, resulting from the reaction of benzhydrylamine and ­epi­chlorohydrin (20), convert into target 23. This constitutes an isolated example of a 4-endo-tet process, which proves its feasibility.[‌38‌]

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