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Dr. Rodolphe Beaud Dr. Bastien Michelet Yasmin Reviriot Dr. Agnès Martin-Mingot Prof. Jean Rodriguez Dr. Damien Bonne Prof. Sébastien Thibaudeau 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2020,132(3):1295-1301
Achieving in a straightforward way the synthesis of enantioenriched elaborated three-dimensional molecules related to bioactive natural products remains a long-standing quest in organic synthesis. Enantioselective organocatalysis potentially offers a unique opportunity to solve this problem, especially when combined with complementary modes of activation. Here, we report the sequential association of organocatalytic and superacid activations of simple linear achiral readily available precursors to promote the formation of unique highly elaborated chiral methylene-bridged benzazocanes exhibiting three to five fully-controlled stereocenters. This peculiar backbone, difficult to assemble by standard synthetic approaches, is closely related to bioactive natural and synthetic morphinans and benzomorphans. The formation of a highly reactive chiral 7-membered ring N-acyl iminium superelectrophilic ion, evidenced by low-temperature in situ NMR experiments, triggers a challenging stereoselective Friedel–Crafts-type cyclization. 相似文献
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Ugo Castelli Jean‐Franois Lohier Ines Drukenmüller Agns Mingot Christian Bachman Carole Alayrac Jrme Marrot Karin Stierstorfer Andreas Kornath Annie‐Claude Gaumont Sbastien Thibaudeau 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2019,131(5):1369-1374
Unambiguously confirmed by low‐temperature in situ NMR experiments, X‐ray diffraction and vibrational spectroscopy, phosphonium‐carbenium superelectrophiles are shown to be generated in strong acidic conditions. Representing crucial intermediates, their exploitation allows for the synthesis of unprecedented fluorinated (cyclic) phosphine oxides. 相似文献
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