Enantioselective Die Is Alder Reaction of 1,2-Dihydropyridines with Aldehydes Using β-Amino Alcohol Organocatalyst

被引：37

作者：

Kohari, Yoshihito ^{[1
]}

Okuyama, Yuko ^{[2
]}

Kwon, Eunsang ^{[3
]}

Furuyama, Taniyuki ^{[4
]}

Kobayashi, Nagao ^{[4
]}

Otuki, Teppei ^{[1
]}

Kumagai, Jun ^{[1
]}

Seki, Chigusa ^{[1
]}

Uwai, Koji ^{[1
]}

Dai, Gang ^{[5
]}

Iwasa, Tatsuo ^{[6
]}

Nakano, Hiroto ^{[1
]}

机构：

[1] Muroran Inst Technol, Grad Sch Engn, Dept Bioengn, Muroran, Hokkaido 0508585, Japan

[2] Tohoku Pharmaceut Univ, Aoba Ku, Sendai, Miyagi 9818585, Japan

[3] Tohoku Univ, Grad Sch Sci, Res & Analyt Ctr Giant Mol, Aoba Ku, Sendai, Miyagi 9808578, Japan

[4] Tohoku Univ, Grad Sch Sci, Dept Chem, Aoba Ku, Sendai, Miyagi 9808578, Japan

[5] Inner Mongolia Normal Univ, Coll Chem & Environm Sci, Hohhot 010022, Inner Mongolia, Peoples R China

[6] Muroran Inst Technol, Grad Sch Engn, Div Engn Composite Funct, Muroran, Hokkaido 0508585, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 20期

基金：

日本科学技术振兴机构;

关键词：

PALLADIUM-PHOSPHINOOXAZOLIDINE CATALYST; CHIRAL ISOQUINUCLIDINES; ALPHA-ACYLOXYACROLEINS; SYNTHETIC METHODOLOGY; ASYMMETRIC-SYNTHESIS; ALKALOIDS; LIGANDS; (+/-)-CATHARANTHINE; ADDITIONS; ALDOL;

D O I：

10.1021/jo501433c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantioselective Diels Alder reaction of 1,2-dihydropyridines with aldehydes using an easily prepared optically active beta-amino alcohol catalyst was found to provide optically active isoquinuclidines, an efficient synthetic intermediate of pharmaceutically important compounds such as oseltamivir phosphate, with a satisfactory chemical yield and enantioselectivity (up to 96%, up to 98% ee). In addition, the obtained highly optically pure isoquinuclidine was easily converted to an optically active piperidine having four successive carbon centers.

引用

页码：9500 / 9511

页数：12

共 39 条

[1] New strategies for organic catalysis: The first highly enantioselective organocatalytic Diels-Alder reaction [J].