Synthesis of Enantioenriched 2-Alkyl Piperidine Derivatives through Asymmetric Reduction of Pyridinium Salts

被引：43

作者：

Qu, Bo ^{[1
]}

Mangunuru, Hari P. R. ^{[1
]}

Wei, Xudong ^{[1
]}

Fandrick, Keith R. ^{[1
]}

Desrosiers, Jean-Nicolas ^{[1
]}

Sieber, Joshua D. ^{[1
]}

Kurouski, Dmitry ^{[1
]}

Haddad, Nizar ^{[1
]}

Samankumara, Lalith P. ^{[1
]}

Lee, Heewon ^{[1
]}

Savoie, Jolaine ^{[1
]}

Ma, Shengli ^{[1
]}

Grinberg, Nelu ^{[1
]}

Sarvestani, Max ^{[1
]}

Yee, Nathan K. ^{[1
]}

Song, Jinhua J. ^{[1
]}

Senanayake, Chris H. ^{[1
]}

机构：

[1] Boehringer Ingelheim Pharmaceut Inc, Chem Dev, 90 E Ridge POB 368, Ridgefield, CT 06877 USA

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 19期

关键词：

HIGHLY ENANTIOSELECTIVE HYDROGENATION; NICOTINIC ACETYLCHOLINE-RECEPTORS; IRIDIUM-CATALYZED HYDROGENATION; STEREOSELECTIVE-SYNTHESIS; MECHANISTIC INVESTIGATIONS; EFFICIENT SYNTHESIS; IMINES; CYCLIZATION;

D O I：

10.1021/acs.orglett.6b02401

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An Ir-catalyzed enantioselective hydrogenation of 2-alkyl-pyridines has been developed using ligand MeO-BoQPhos. High levels of enantioselectivities up to 93:7 er were obtained. The resulting enantioenriched piperidines can be readily converted into biologically interesting molecules such as the fused tricyclic structures 5, 6, and 7 in 99:1 er, providing a novel, concise synthetic route to this family of chiral piperidine-containing compounds.

引用

页码：4920 / 4923

页数：4

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