TY - JOUR
T1 - Highly enantioselective synthesis of isoquinuclidine by diels-alder reaction of 1,2-dihydropyridine utilizing chiral bisoxazoline-Cu(II) complex
AU - Hutabarat, N. D.M.Romauli
AU - Seki, Chigusa
AU - Shimizu, Takashi
AU - Hirama, Masafumi
AU - Kohari, Yoshihito
AU - Nakano, Hiroto
AU - Uwai, Koji
AU - Takano, Nobuhiro
AU - Kwon, Eunsang
AU - Matsuyama, Haruo
PY - 2012
Y1 - 2012
N2 - The enantioselective Diels-Alder (D-A) reaction between N-phenoxycarbonyl- or N-benzyloxycarbonyl-1,2-dihydropyridine (1a or 1b) and N(2)-acryloyl-N(1)-(1- naphthylmethyl)-5,5-dimethylpyrazolidin-3-one (2b) using (S,S)-bisoxazoline- Cu(II) catalyst (A, B, C or D) has been investigated. Utilizing (S,S)-t-Bu-bisoxazoline-Cu(II) catalyst C, the D-A reaction of 1a and 2 afforded the endo-(7S)-isoquinuclidines (3, 4 or 5) in good chemical yields with high enantioselectivity (up to 99% e.e.).
AB - The enantioselective Diels-Alder (D-A) reaction between N-phenoxycarbonyl- or N-benzyloxycarbonyl-1,2-dihydropyridine (1a or 1b) and N(2)-acryloyl-N(1)-(1- naphthylmethyl)-5,5-dimethylpyrazolidin-3-one (2b) using (S,S)-bisoxazoline- Cu(II) catalyst (A, B, C or D) has been investigated. Utilizing (S,S)-t-Bu-bisoxazoline-Cu(II) catalyst C, the D-A reaction of 1a and 2 afforded the endo-(7S)-isoquinuclidines (3, 4 or 5) in good chemical yields with high enantioselectivity (up to 99% e.e.).
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UR - http://www.scopus.com/inward/citedby.url?scp=84880617390&partnerID=8YFLogxK
U2 - 10.3987/COM-12-S(N)2
DO - 10.3987/COM-12-S(N)2
M3 - Article
AN - SCOPUS:84880617390
SN - 0385-5414
VL - 86
SP - 203
EP - 217
JO - Heterocycles
JF - Heterocycles
IS - 1
ER -