LiAlH4-Induced Selective Ring Rearrangement of 2-(2-Cyanoethyl)aziridines toward 2-(Aminomethyl)pyrrolidines and 3-Aminopiperidines as Eligible Heterocyclic Building Blocks

被引：21

作者：

Dolfen, Jeroen ^{[1
]}

Vervisch, Karel ^{[1
]}

De Kimpe, Norbert ^{[1
]}

D'hooghe, Matthias ^{[1
]}

机构：

[1] Univ Ghent, Fac Biosci Engn, Dept Sustainable Organ Chem & Technol, SynBioC Res Grp, Coupure Links 653, B-9000 Ghent, Belgium

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2016年 / 22卷 / 14期

关键词：

aziridines; bicyclic systems; Lewis acids; piperidines; pyrrolidines; ANDROGEN RECEPTOR MODULATORS; ASYMMETRIC-SYNTHESIS; CHIRAL AZIRIDINES; GAMMA-LACTONES; PIPERIDINES; PRECURSORS; EPOXIDES; SCAFFOLD; POTENT; TRANSFORMATION;

D O I：

10.1002/chem.201504853

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

2-(2-Cyanoethyl)aziridines and 2-aryl-3-(2-cyanoethyl)aziridines were deployed as substrates for an In(OTf)(3)-mediated regio- and stereoselective ring rearrangement upon treatment with LiAlH4, affording a variety of novel 2-(aminomethyl)pyrrolidines and 3-aminopiperidines, respectively. Further synthetic elaboration of the obtained 3-aminopiperidines resulted in the formation of a peculiar and unexplored conformationally constrained imidazolidinone and diketopiperazine scaffold.

引用

页码：4945 / 4951

页数：7

共 51 条

[1] A direct stereoselective approach to trans-2,3-disubstituted piperidines:: Application in the synthesis of 2-epi-CP-99,994 and (+)-epilupinine [J].

Ahari, M'hamed ;

Perez, Amandine ;

Menant, Christine ;

Vasse, Jean-Luc ;

Szymoniak, Jan .

ORGANIC LETTERS, 2008, 10 (12) :2473-2476

[2] A NEW CHIRAL SYNTHESIS OF WIELAND-MIESCHER KETONE CATALYZED BY A COMBINATION OF (S)-N-BENZYL-N-(2-PYRROLIDINYLMETHYL)AMINE DERIVATIVE AND BRONSTED ACID [J].

Akahane, Yuichi ;

Inomata, Kohei ;

Endo, Yasuyuki .

HETEROCYCLES, 2009, 77 (02) :1065-1078

[3] Synthesis of chiral diamines using novel 2-trichloromethyloxazolidin-4-one precursors derived from 5-oxo-proline and proline [J].

Amedjkouh, M ;

Ahlberg, P .

TETRAHEDRON-ASYMMETRY, 2002, 13 (20) :2229-2234

[4] RULES FOR RING-CLOSURE [J].

BALDWIN, JE .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) :734-736

[5] INTRAMOLECULAR AMINOMERCURATION OF CYCLOOCTENE AZIRIDINES AND AMINO ALCOHOL PRECURSORS [J].

BARRELLE, M ;

APPARU, M .

TETRAHEDRON, 1977, 33 (11) :1309-1319

[6] The formation and stabillity of spiro-compounds. Part I. Spiro-compounds from cyclo-hexane. [J].

Beesley, RM ;

Ingold, CK ;

Thorpe, JF .

JOURNAL OF THE CHEMICAL SOCIETY, 1915, 107 :1080-1106

[7] Asymmetric Transfer Hydrogenation of 3-Nitroquinolines: Facile Access to Cyclic Nitro Compounds with Two Contiguous Stereocenters [J].

Cai, Xian-Feng ;

Chen, Mu-Wang ;

Ye, Zhi-Shi ;

Guo, Ran-Ning ;

Shi, Lei ;

Li, Yan-Qin ;

Zhou, Yong-Gui .

CHEMISTRY-AN ASIAN JOURNAL, 2013, 8 (07) :1381-1385

[8] Synthesis and Reactivity of 2-(Carboxymethyl)aziridine Derivatives [J].

Callebaut, Gert ;

Meiresonne, Tamara ;

De Kimpe, Norbert ;

Mangelinckx, Sven .

CHEMICAL REVIEWS, 2014, 114 (16) :7954-8015

[9] One step synthesis of sulfur and nitrogen linked aza-disaccharide precursors from D-mannitol derived bis-aziridines [J].

Campanini, L ;

Dureault, A ;

Depezay, JC .

TETRAHEDRON LETTERS, 1996, 37 (29) :5095-5098

[10] Directed ortho lithiation of N-alkylphenylaziridines [J].

Capriati, V ;

Florio, S ;

Luisi, R ;

Musio, B .

ORGANIC LETTERS, 2005, 7 (17) :3749-3752

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