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Triethylamine Enables Catalytic Generation of Oxidopyrylium Ylides for [5+2] Cycloadditions with Alkenes: An Efficient Entry to 8‐Oxabicyclo[3.2.1]octane Frameworks
Author(s) -
Toda Yasunori,
Shimizu Masahiro,
Iwai Taichi,
Suga Hiroyuki
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201800290
Subject(s) - chemistry , triethylamine , octane , cycloaddition , intramolecular force , intermolecular force , ylide , catalysis , azomethine ylide , intramolecular reaction , organic chemistry , combinatorial chemistry , 1,3 dipolar cycloaddition , molecule
An efficient method for the preparation of a range of 8‐oxabicyclo[3.2.1]octane derivatives including synthetic intermediates of natural products is described, in which triethylamine effectively catalyzes [5+2] cycloaddition reactions between oxidopyrylium ylides and alkenes. This method can be applied not only to intermolecular cycloadditions with various alkenes but also to intramolecular cycloadditions. The key finding is that the combined use of organic bases having appropriate basicity and oxidopyrylium ylide precursors bearing a suitable leaving group facilitates the base‐assisted generation of oxidopyrylium ylides in a catalytic manner.