TY - JOUR
T1 - Highly enantioselective catalytic asymmetric Mukaiyama-Michael reactions of cyclic α-alkylidene β-oxo imides
AU - Oyama, Harufumi
AU - Orimoto, Kohei
AU - Niwa, Takashi
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 - 2015/3/28
Y1 - 2015/3/28
N2 - Abstract Catalytic asymmetric Mukaiyama-Michael reactions of cyclic α-alkylidene β-oxo imides are described. The rationally designed cyclic α-alkylidene β-oxo imides show high enantioselectivity in the Mukaiyama-Michael reaction using a bisoxazoline/Cu(OTf)2 catalyst. The enantioselectivity can be well explained by the chelate model comprising an intramolecular hydrogen bond, wherein the cyclic α-alkylidene β-oxo imide coordinates with Cu(II) through the two imide carbonyls.
AB - Abstract Catalytic asymmetric Mukaiyama-Michael reactions of cyclic α-alkylidene β-oxo imides are described. The rationally designed cyclic α-alkylidene β-oxo imides show high enantioselectivity in the Mukaiyama-Michael reaction using a bisoxazoline/Cu(OTf)2 catalyst. The enantioselectivity can be well explained by the chelate model comprising 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.2015.01.012
DO - 10.1016/j.tetasy.2015.01.012
M3 - Article
AN - SCOPUS:84939933919
SN - 0957-4166
VL - 26
SP - 262
EP - 270
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
IS - 5-6
M1 - 59259
ER -