Regioselective Ring-Opening of Amino Acid-Derived Chiral Aziridines: an Easy Access to cis-2,5-Disubstituted Chiral Piperazines

被引：27

作者：

Samanta, Krishnananda ^{[1
]}

Panda, Gautam ^{[1
]}

机构：

[1] Cent Drug Res Inst, Div Med & Proc Chem, Lucknow 226001, Uttar Pradesh, India

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2011年 / 6卷 / 01期

关键词：

amino acids; cyclization; heterocycles; natural products; regioselectivity; MITSUNOBU; POTENT; INHIBITORS; CHEMISTRY;

D O I：

10.1002/asia.201000554

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient four-step synthetic strategy for cis-2,5-disubstituted chiral piperazines derived from amino-acid-based aziridines is described. The key steps in this strategy are the highly regioselective boron trifluoride diethyl etherate (BF3 center dot OEt2)-mediated ring-opening of less-reactive N-Ts chiral aziridines by alpha-amino acid methyl ester hydrochloride followed by Mitsunobu cyclization. This protocol has been used in an attempt to construct the piperazine core framework of natural product (+)-piperazinomycin.

引用

页码：189 / 197

页数：9

共 54 条

[1] A new approach to the synthesis of piperazinomycin and bouvardin: Facile access to cycloisodityrosine via an intramolecular SNAr reaction [J].

Beugelmans, R ;

Bigot, A ;

BoisChoussy, M ;

Zhu, JP .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (02) :771-774

[2] TOTAL SYNTHESIS OF (+)-PIPERAZINOMYCIN [J].

BOGER, DL ;

ZHOU, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (24) :11426-11433

[3] Microwave-assisted ring-opening of activated aziridines with resin-bound amines [J].

Crestey, Francois ;

Witt, Matthias ;

Frydenvang, Karla ;

Staerk, Dan ;

Jaroszewski, Jerzy W. ;

Franzyk, Henrik .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (09) :3566-3569

[4] Expedite Protocol for Construction of Chiral Regioselectively N-Protected Monosubstituted Piperazine, 1,4-Diazepane, and 1,4-Diazocane Building Blocks [J].

Crestey, Francois ;

Witt, Matthias ;

Jaroszewski, Jerzy W. ;

Franzyk, Henrik .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (15) :5652-5655

[5] A new route to 1,4-oxazepanes and 1,4-diazepanes from Garner aldehyde [J].

Das, Sanjit Kumar ;

Srivastava, Ajay Kumar ;

Panda, Gautam .

TETRAHEDRON LETTERS, 2010, 51 (11) :1483-1485

[6] Syntheses and transformations of piperazinone rings. A review [J].

Dinsmore, CJ ;

Beshore, DC .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2002, 34 (04) :367-+

[7] L-735,524 - THE DESIGN OF A POTENT AND ORALLY BIOAVAILABLE HIV PROTEASE INHIBITOR [J].

DORSEY, BD ;

LEVIN, RB ;

MCDANIEL, SL ;

VACCA, JP ;

GUARE, JP ;

DARKE, PL ;

ZUGAY, JA ;

EMINI, EA ;

SCHLEIF, WA ;

QUINTERO, JC ;

LIN, JH ;

CHEN, IW ;

HOLLOWAY, MK ;

FITZGERALD, PMD ;

AXEL, MG ;

OSTOVIC, D ;

ANDERSON, PS ;

HUFF, JR .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (21) :3443-3451

[8] BF3•OEt2-Mediated Highly Regioselective SN2-Type Ring-Opening of N-Activated Aziridines and N-Activated Azetidines by Tetraalkylammonium Halides [J].

Ghorai, Manas K. ;

Kumar, Amit ;

Tiwari, Deo Prakash .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (01) :137-151

[9] Enantioselective Syntheses of Morpholines and Their Homologues via SN2-Type Ring Opening of Aziridines and Azetidines with Haloalcohols [J].

Ghorai, Manas K. ;

Shukla, Dipti ;

Das, Kalpataru .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (18) :7013-7022

[10] STRUCTURE-ACTIVITY-RELATIONSHIPS IN PRAZOSIN-RELATED COMPOUNDS .2. ROLE OF THE PIPERAZINE RING ON ALPHA-BLOCKING ACTIVITY [J].

GIARDINA, D ;

GULINI, U ;

MASSI, M ;

PILONI, MG ;

POMPEI, P ;

RAFAIANI, G ;

MELCHIORRE, C .

JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (06) :690-698

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