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DOI:
10.1055/sos-SD-140-00195
Couty, F., Science of Synthesis Knowledge Updates, (2017) 2, 456.
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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References
[38] | Meeeeee Meeee, M. M. M. M.; Meee, M. M.; Meeeee, M.; Meeeeeeeeee, M.; Meeeeeeeeee, M.; Meeeeeee, M., Mee. Meeeeee Mee. Mee., (8888) 88, 888. |