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

共 82 条

[71]

Reddy LR, 2001, NEW J CHEM, V25, P221

[72] Opening of epoxides with aromatic amines promoted by indium tribromide:: a mild and efficient method for the synthesis of β-amino alcohols [J].

Rodríguez, JR ;

Navarro, A .

TETRAHEDRON LETTERS, 2004, 45 (40) :7495-7498

[73] Synthesis of β-amino alcohols by regioselective ring opening of arylepoxides with anilines catalyzed by cobaltous chloride [J].

Sundararajan, G ;

Vijayakrishna, K ;

Varghese, B .

TETRAHEDRON LETTERS, 2004, 45 (44) :8253-8256

[74] Practical synthesis of structurally important spirodiamine templates [J].

Tang, F. -Y. ;

Qu, L. -Q. ;

Xu, Y. ;

Ma, R. -J. ;

Chen, S. -H. ;

Li, G. .

SYNTHETIC COMMUNICATIONS, 2007, 37 (19-21) :3793-3799

[75]

Targum S., 1995, Eur. Neuropsychopharmacol, V5, P4

[76] A new approach towards 1-phenyl and 1-benzyl substituted 2-(aminomethyl)cyclopropanecarboxamides as novel derivatives of the antidepressant Milnacipran [J].

Vervisch, Karel ;

D'hooghe, Matthias ;

Tornroos, Karl W. ;

De Kimpe, Norbert .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (16) :3271-3279

[77]

Vila X, 2006, HETEROCYCLES, V70, P45

[78] Nitrile hydrolysis activity of rhodococcus erythropolis NCIMB 11540 whole cells [J].

Vink, Mandy K. S. ;

Wijtmans, Roel ;

Reisinger, Christoph ;

van den Berg, Rutger J. F. ;

Schortinghuis, Christien A. ;

Schwab, Helmut ;

Schoemaker, Hans E. ;

Rutjes, Floris P. J. T. .

Biotechnology Journal, 2006, 1 (05) :569-573

[79] A stereodivergent approach to substituted 4-hydroxypiperidines [J].

Vink, MKS ;

Schortinghuis, CA ;

Luten, J ;

van Maarseveen, JH ;

Schoemaker, HE ;

Hiemstra, H ;

Rutjes, FPJT .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (22) :7869-7871

[80] A diastereoselective synthesis of 2,4-disubstituted piperidines: Scaffolds for drug discovery [J].

Watson, PS ;

Jiang, B ;

Scott, B .

ORGANIC LETTERS, 2000, 2 (23) :3679-3681

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