Stereoselective synthesis of optically active cyclopenta[c]pyridines and tetrahydropyridines

被引：10

作者：

Sezer, Serdar ^{[1
]}

Gumrukcu, Yasemin ^{[1
]}

Bakirci, Irem ^{[1
]}

Unver, M. Yagiz ^{[1
]}

Tanyeli, Cihangir ^{[1
]}

机构：

[1] Middle E Tech Univ, Dept Chem, TR-06800 Ankara, Turkey

来源：

TETRAHEDRON-ASYMMETRY | 2012年 / 23卷 / 09期

关键词：

PAUSON-KHAND REACTION; ALKENE ALKYNE CYCLIZATIONS; ENANTIOMERIC SEPARATION; MITSUNOBU REACTION; FORMAL SYNTHESIS; COMPLEXES; ALKALOIDS; ACID; ALLENYLBORATION; AMINES;

D O I：

10.1016/j.tetasy.2012.04.016

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The intramolecular Pauson-Khand and ring closing metathesis (RCM) reactions of nitrogen containing chiral enynes and dienes are described. The enyne and diene systems comprised of N-propargylated and N-allylated units are constructed on chiral homoallylic or homopropargylic alcohol backbones, respectively, via S(N)2 and/or modified Mitsunobu reactions. The racemic homoallylic and homopropargylic alcohol derivatives were successfully resolved in high ee (93-99%) by applying chemoenzymatic methods using various lipases such as PS-C II, Lipozyme, and CAL-B. Each enantiomerically enriched enyne afforded the most conformationally stable diastereomeric cyclopenta[c]pyridine ring system as the sole product, whereas enantiomerically enriched dienes gave tetrahydropyridine derivatives as a result of intramolecular Pauson-Khand and RCM reactions, respectively. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：662 / 669

页数：8

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