In 2015,Wang, Zhaobin; Sheong, Fu Kit; Sung, Herman H. Y.; Williams, Ian D.; Lin, Zhenyang; Sun, Jianwei published 《Catalytic Enantioselective Intermolecular Desymmetrization of Azetidines》.Journal of the American Chemical Society published the findings.Electric Literature of C3H8ClNO The information in the text is summarized as follows:
The first catalytic asym. desymmetrization of azetidines is disclosed. Despite the low propensity of azetidine ring opening and challenging stereocontrol, smooth intermol. reactions were realized with excellent efficiency and enantioselectivity. These were enabled by the suitable combination of catalyst, nucleophile, protective group, and reaction conditions. The highly enantioenriched densely functionalized products are versatile precursors to other useful chiral mols. Mechanistic studies, including DFT calculations, revealed that only one catalyst mol. is involved in the key transition state, though both reactants can be activated. Also, the Curtin-Hammett principle dictates the reaction proceeds via amide nitrogen activation. The experimental part of the paper was very detailed, including the reaction process of Azetidin-3-ol hydrochloride(cas: 18621-18-6Electric Literature of C3H8ClNO)
Azetidin-3-ol hydrochloride(cas:18621-18-6) is one of azetidine.Azetidines (azacyclobutanes) constitute a well-known class of heterocyclic compounds. Azetidine scaffold has been discovered in several natural products.Electric Literature of C3H8ClNO Several pharmacologically important synthetic compounds also contain azetidine ring. Because of inherent ring strain, the synthesis of azetidines is a challenging endeavor.
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