Dearomative [4 + 3] cycloaddition of furans with vinyl-N-triftosylhydrazones by silver catalysis: stereoselective access to oxa-bridged seven-membered bicycles
Keyword(s):
Abstract The first example of dearomative [4 + 3] cycloaddition between furans and vinyl-N-sulfonylhydrazones as vinylcarbene precursors is reported. The merger of silver catalysis and easily decomposable vinyl-N-triftosylhydrazones enabled the efficient synthesis of a variety of skeletally and functionally diverse oxa-bridged seven-membered bicyclic compounds with complete and predictable stereoselectivity. The combination of experimental studies and DFT calculations disclosed that the silver-catalyzed reaction proceeds via a concerted [4 + 3] cycloaddition mechanism, rather than the generally accepted cyclopropanation / Cope rearrangement pathway by rhodium catalysis.
2020 ◽
2021 ◽
Keyword(s):
2019 ◽
Vol 9
(22)
◽
pp. 6327-6334
◽
Keyword(s):
Keyword(s):
Isoxazolium N-ylides and 1-oxa-5-azahexa-1,3,5-trienes on the way from isoxazoles to 2H-1,3-oxazines
2014 ◽
Vol 10
◽
pp. 1896-1905
◽
1990 ◽
Vol 112
(1)
◽
pp. 260-264
◽