Lewis Acids Promoted
3 + 2 Cycloaddition of Oxaziridines
and Cyclic Allylic Alcohols through Carbonyl Imine Intermediates
Erbao Zhao
Feilong Zhou
Yujun Zhao
10.1021/acs.joc.9b00246.s004
https://acs.figshare.com/articles/dataset/Lewis_Acids_Promoted_3_2_Cycloaddition_of_Oxaziridines_and_Cyclic_Allylic_Alcohols_through_Carbonyl_Imine_Intermediates/7887473
Syntheses of isoxazolidines through
the carbonyl imine intermediates
are currently limited to monosubstituted olefin substrates. Herein,
we reported syntheses of novel bicyclic isoxazolidine-containing compounds
through 1,3-dipolar cycloaddition reactions using cyclic allylic alcohols
as substrates, which proved challenging in previous reports. Generally,
the reaction yields range from good to high, and the reaction substrates
tolerate various functional groups, including the cyclopropyl and
amine groups. Mechanistic studies suggest that an allylic cation and
a carbonyl imine intermediate are involved and responsible for the
observed stereochemistry and diastereoselectivity.
2019-03-14 00:00:00
carbonyl imine intermediates
Carbonyl Imine Intermediates Syntheses
reaction substrates
2 Cycloaddition
Cyclic Allylic Alcohols
monosubstituted olefin substrates
Mechanistic studies
cyclic allylic alcohols
allylic cation
carbonyl imine
reaction yields range
novel bicyclic isoxazolidine-containing compounds
Lewis Acids Promoted 3
amine groups