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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 31, 2001 - Issue 17
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Original Articles

L-ALANINE BENZYLESTER AS CHIRAL INDUCTOR: SYNTHESIS OF ENANTIOPURE PYRAZOLO[1,5-a]-[1,4]BENZODIAZEPINE-4-ONES VIA INTRAMOLECULAR NITRILIMINE CYCLOADDITIONS

Gianluigi Broggini Dipartimento di Scienze Chimiche, Fisiche e Matematiche, Università dell'Insubria, via Lucini 3, Como, 22100, Italy
,
Luisa Garanti Dipartimento di Chimica Organica e Industriale, Università di Milano, via Golgi 19, Milano, 20133, Italy
,
Giorgio Molteni Dipartimento di Chimica Organica e Industriale, Università di Milano, via Golgi 19, Milano, 20133, Italy
&
Tullio Pilati Dipartimento di Chimica Organica e Industriale, Università di Milano, via Golgi 19, Milano, 20133, Italy
Pages 2649-2656 | Received 02 Aug 2000, Published online: 09 Nov 2006
 
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Abstract

The title compounds, of potential pharmacological interest, have been obtained in the enantiopure form through a stereoselective intramolecular 1,3-dipolar cycloaddition of homochiral nitrilimines 5.

ACKNOWLEDGMENT

We are grateful to CNR and MURST for financial support.

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Related Research Data

CCDC 147229: Experimental Crystal Structure Determination
Source: Cambridge Crystallographic Data Centre
The first example of a (1R,2S,5R)-(−)-menthyl chiral auxiliary in intramolecular nitrilimine cycloadditions: synthesis of enantiopure pyrazolo[1,5-a][4,1]benzoxazepines and pyrazolo[1,5-a][4,1]benzodiazepines
Source: Elsevier BV
Stereoselective intramolecular cycloadditions of homochiral nitrile imines: synthesis of enantiomerically pure 3,3a-dihydro-pyrazolo[1,5-a][1,4]benzodiazepine-6(4H)-ones
Source: Elsevier BV
Diastereoselective synthesis of bis(3,5)pyrazolophanes by sequential inter- and intramolecular cycloadditions of homochiral nitrilimines
Source: Elsevier BV
The first case of asymmetric induction in intramolecular nitrile imine cycloadditions: synthesis of enantiopure 3-substituted 6-oxo-2,3,3a,5-tetrahydro-4-carbomethoxy-furo[3,4-c]pyrazoles
Source: Elsevier BV
Asymmetric induction by the (S)-1-phenylethyl group in intramolecular nitrile imine cycloadditions giving enantiopure 3,3a-dihydro-pyrazolo[1,5-a][1,4]benzodiazepine-4(6H)-ones
Source: Elsevier BV

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