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Inherently Chiral Cavitand Curvature: Diastereoselective Oxidation of Tethered Allylsilanes
Author(s) -
Inoue Mami,
Fujii Yoshino,
Matsumoto Yasuhiro,
Schramm Michael P.,
Iwasawa Tetsuo
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900891
Subject(s) - cavitand , chemistry , diastereomer , methylene , epoxide , yield (engineering) , stereochemistry , molecule , group (periodic table) , supramolecular chemistry , medicinal chemistry , organic chemistry , catalysis , materials science , metallurgy
Syntheses of inwardly and outwardly directed allylsilanes those are tethered to new inherently chiral cavitands are described. Oxidized with mCPBA, these allylsilanes result in diastereomeric mixtures of epoxide molecules. Thus, it enables us to have comparative study of cavitand‐structure diastereoselectivity relationship, which revealed that an inward allylsilane group flanked by a dibenzo[ f, h ]quinoxaline and two bridged methylene groups have the best chemical yield and diastereoselection.