A simple stereoselective synthesis of enantiopure 2-substituted pyrrolidines and piperidines from chiral (R)-phenylglycinol-derived bicyclic 1,3-oxazolidines

被引：0

作者：

Andrés, JM ^{[1
]}

Herráiz-Sierra, I ^{[1
]}

Pedrosa, R ^{[1
]}

Pérez-Encabo, A ^{[1
]}

机构：

[1] Univ Valladolid, Fac Ciencias, Dept Quim Organ, E-47011 Valladolid, Spain

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2000年 / 2000卷 / 09期

关键词：

asymmetric synthesis; nitrogen heterocycles; heterocycles; pyrrolidines; piperidines;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral, nonracemic 2-substituted pyrrolidines and piperidines were prepared in high ee and moderate to good chemical yields in three steps from (R)-phenylglycinol and gamma- or delta-chloroketones. The key step of the synthesis was the stereo-selective reductive ring-opening of chiral bicyclic 1,3-oxazolidines prepared by condensation of (R)-phenylglycinol and the corresponding ketones.

引用

页码：1719 / 1726

页数：8

共 21 条

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JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (06): : 2792 - 2802
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Higashiyama, K
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CHEMISTRY LETTERS, 1998, (02) : 119 - 120
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Ward, Amanda F.
Wolfe, John P.
ORGANIC LETTERS, 2011, 13 (17) : 4728 - 4731
[6] Application of meso-hydrobenzoin-derived chiral auxiliaries for the stereoselective synthesis of highly substituted pyrrolidines by 1,3-dipolar cycloaddition of azomethine ylides
Bica, Katharina
Gaertner, Peter
TETRAHEDRON-ASYMMETRY, 2010, 21 (06) : 641 - 646
[7] ASYMMETRIC ALPHA-SUBSTITUTED PHENETHYLAMINES .5. SYNTHESIS OF CHIRAL 1-ALKYL-2-PHENYLETHYLAMINES VIA GRIGNARD REACTION OF 4-PHENYL-1,3-OXAZOLIDINES
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HIGASHIYAMA, K
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CHEMICAL & PHARMACEUTICAL BULLETIN, 1985, 33 (11) : 4662 - 4670
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JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (19): : 2791 - 2794
[9] Synthesis and Anti-Proliferative Activity of Novel Tricyclic Compounds Derived from 2-Substituted 1,3-Indandione
H. S. Abd-Elghaffar
M. A. El-Hashash
S. F. Mohamed
A. A. Ibrahim
A. E. Amr
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Russian Journal of General Chemistry, 2020, 90 : 686 - 696
[10] Synthesis and Anti-Proliferative Activity of Novel Tricyclic Compounds Derived from 2-Substituted 1,3-Indandione
Abd-Elghaffar, H. S.
El-Hashash, M. A.
Mohamed, S. F.
Ibrahim, A. A.
Amr, A. E.
Al-Omar, M. A.
Nossier, E. S.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2020, 90 (04) : 686 - 696

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