TY - JOUR
T1 - Enantioselective Formal [3+2] Cycloaddition of Epoxides with Imines under Brønsted Base Catalysis
T2 - Synthesis of 1,3-Oxazolidines with Quaternary Stereogenic Center
AU - Kondoh, Azusa
AU - Akahira, Shiori
AU - Oishi, Masafumi
AU - Terada, Masahiro
PY - 2018/5/22
Y1 - 2018/5/22
N2 - The formal [3+2] cycloaddition of epoxides and unsaturated compounds is a powerful methodology for the synthesis of densely functionalized five-membered heterocyclic compounds containing oxygen. Described is a novel enantioselective formal [3+2] cycloaddition of epoxides under Brønsted base catalysis. The bis(guanidino)iminophosphorane as a chiral organosuperbase catalyst enabled the enantioselective reaction of β,γ-epoxysulfones with imines, owing to its strong basicity and high stereocontrolling ability, to provide enantioenriched 1,3-oxazolidines having two stereogenic centers, including a quaternary one, in a highly diastereo- and enantioselective manner.
AB - The formal [3+2] cycloaddition of epoxides and unsaturated compounds is a powerful methodology for the synthesis of densely functionalized five-membered heterocyclic compounds containing oxygen. Described is a novel enantioselective formal [3+2] cycloaddition of epoxides under Brønsted base catalysis. The bis(guanidino)iminophosphorane as a chiral organosuperbase catalyst enabled the enantioselective reaction of β,γ-epoxysulfones with imines, owing to its strong basicity and high stereocontrolling ability, to provide enantioenriched 1,3-oxazolidines having two stereogenic centers, including a quaternary one, in a highly diastereo- and enantioselective manner.
KW - Brønsted base
KW - asymmetric catalysis
KW - cycloaddition
KW - heterocycles
KW - organocatalysis
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U2 - 10.1002/anie.201802468
DO - 10.1002/anie.201802468
M3 - Article
C2 - 29645337
AN - SCOPUS:85046022458
VL - 57
SP - 6299
EP - 6303
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
SN - 1433-7851
IS - 21
ER -