TY - JOUR
T1 - Highly enantioselective catalytic Friedel-Crafts reactions of cyclic α-alkylidene β-oxo imides
AU - Oyama, Harufumi
AU - Nakada, Masahisa
N1 - Funding Information:
This work was financially supported in part by The Grant-in-Aid for Scientific Research (B) ( 25293003 ) by MEXT , Japan and a Waseda University Grant for Special Research Projects.
Publisher Copyright:
©2015 Elsevier Ltd. All rights reserved.
PY - 2015/2/28
Y1 - 2015/2/28
N2 - Highly enantioselective catalytic Friedel-Crafts reactions of cyclic α-alkylidene β-oxo imides with indole, pyrrole, and furan derivatives at relatively low temperatures are described. The X-ray crystallographic analysis of the product revealed that the sense of enantioselectivity of the Friedel-Crafts reactions could be well explained by the proposed chelate model. The model was stabilized by an intramolecular hydrogen bond, wherein the cyclic α-alkylidene β-oxo imide coordinates with Cu(II) through the two imide carbonyls.
AB - Highly enantioselective catalytic Friedel-Crafts reactions of cyclic α-alkylidene β-oxo imides with indole, pyrrole, and furan derivatives at relatively low temperatures are described. The X-ray crystallographic analysis of the product revealed that the sense of enantioselectivity of the Friedel-Crafts reactions could be well explained by the proposed chelate model. The model was stabilized by an intramolecular hydrogen bond, wherein the cyclic α-alkylidene β-oxo imide coordinates with Cu(II) through the two imide carbonyls.
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U2 - 10.1016/j.tetasy.2015.01.004
DO - 10.1016/j.tetasy.2015.01.004
M3 - Article
AN - SCOPUS:84922810044
SN - 0957-4166
VL - 26
SP - 195
EP - 202
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
IS - 4
ER -