Synthesis of Stereodefined Piperidines from Aziridines and Their Transformation into Conformationally Constrained Amino Acids, Amino Alcohols and 2,7-Diazabicyclo[3.3.1]nonanes

被引：32

作者：

Vervisch, Karel ^{[1
]}

D'hooghe, Matthias ^{[1
]}

Tornroos, Karl W. ^{[2
]}

De Kimpe, Norbert ^{[1
]}

机构：

[1] Univ Ghent, Dept Sustainable Organ Chem & Technol, Fac Biosci Engn, B-9000 Ghent, Belgium

[2] Univ Bergen, Dept Chem, N-5007 Bergen, Norway

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 22期

关键词：

RING-OPENING REACTIONS; ASYMMETRIC-SYNTHESIS; EFFICIENT METHOD; DERIVATIVES; CHEMISTRY; SALTS; AFFINITY; RECEPTOR; ANALOGS; 1-ALKYL-2-(BROMOMETHYL)AZIRIDINES;

D O I：

10.1021/jo101646u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-(2-Cyano-2-phenylethyl)azindines were converted into novel cis- and trans-2-chloromethyl-4-phenylpiperidine-4-carbonitriles via alkylation with 1-bromo-2-chloroethane followed by microwave-assisted 6-exo-tet cyclization and regiospecific ring opening The latter piperidines were used as eligible substrates for the synthesis of stereodefined 2-chloromethyl-, 2-hydroxymethyl-, and 2-carboxymethyl-4-phenylpiperidine-4-carboxylic acids, 2-hydroxymethyl-4-phenylpiperidine-4-carbonitriles, 3-hydroxy-5-phenylazepane-5-carbonitriles, and 5-phenyl-2,7-diazabicyclo[3 3 1]nonanes

引用

页码：7734 / 7744

页数：11

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