An Unusual and Stereoselective Michael Addition of αAmino Ester-Derived N-Lithiated Azomethine Ylides

Adrien Soret; Luis Blanco; Sandrine Deloisy

doi:10.2174/157017806778700006

ISSN: 1570-1786
E-ISSN: 1875-6255

An Unusual and Stereoselective Michael Addition of αAmino Ester-Derived N-Lithiated Azomethine Ylides
Authors: Adrien Soret¹, Luis Blanco² and Sandrine Deloisy³
View Affiliations Hide Affiliations

¹ Laboratoire de Synthese Organique et Methodologie, Institut de Chimie Moleculaire et des Materiaux d'Orsay (UMR 8182), Bat. 420, Universite de Paris-Sud, 91405 Orsay Cedex, France. ² Laboratoire de Synthese Organique et Methodologie, Institut de Chimie Moleculaire et des Materiaux d'Orsay (UMR 8182), Bat. 420, Universite de Paris-Sud, 91405 Orsay Cedex, France. ³ Laboratoire de Synthese Organique et Methodologie, Institut de Chimie Moleculaire et des Materiaux d'Orsay (UMR 8182), Bat. 420, Universite de Paris-Sud, 91405 Orsay Cedex, France.
Source: Letters in Organic Chemistry, Volume 3, Issue 9, Sep 2006, p. 648 - 653
DOI: https://doi.org/10.2174/157017806778700006
- Available online: 01 Sep 2006

Abstract

N-Lithiated azomethine ylides generated from N-arylidene-α-amino esters react on their C&ggr:-atom with a 7-oxabicyclo[2.2.1]heptadiene derived diester. This regio- and stereoselective Michael addition yields β-amino diesters after acidic work-up. Retro-Diels-Alder reaction from these amines or related amides allows the preparation of (aminomethyl)maleate derivatives.

Article metrics loading...

/content/journals/loc/10.2174/157017806778700006

2006-09-01

2025-10-06

From This Site

/content/journals/loc/10.2174/157017806778700006

dcterms_title,dcterms_subject,pub_keyword

-contentType:Contributor -contentType:Concept -contentType:Institution

10

5

Full text loading...

/content/journals/loc/10.2174/157017806778700006

Article Type: Research Article

Keyword(s): 1,3-dipolar cycloaddition; Azomethine ylides; Michael addition; N-arylidene-a-amino esters; retro-Diels-Alder reaction

An Unusual and Stereoselective Michael Addition of αAmino Ester-Derived N-Lithiated Azomethine Ylides

Abstract

From This Site

Most Read This Month

Most Cited Most Cited RSS feed

Vilsmeier-Haack Cyclisation as a Facile Synthetic Route to Thieno [2,3- b] Quinolines (Part I)

Efficient Synthesis of 4-Arylmethylene-3-methylisoxazol-5(4H)-one Derivatives Catalyzed by Malic Acid

Wonderful Natural Drugs with Surprising Nutritional Values, Rheum Species, Gifts of the Nature

Novel Derivatives Based on Zerumbone Scaffold as Potential Anticancer Inhibitors

A Review on the Syntheses and Applications of the 5H-chromeno[2,3- b]pyridines

Fe Doped Ga2O3 Nanomaterial Catalysed Green and Efficient One Pot Three Component Synthesis of Tetrahydrobenzo[b]pyran

Sulfonated Ethylenediamine Functionalized Magnetic Nanoparticles as a Highly Efficient Heterogeneous Nanocatalyst for the Green Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones

K2CO3/TBAB, a Composite of Inorganic and Organic Salts, a Novel and Powerful Media for Regioselective Michael Addition of Dihydropyrimidinones to Acrylic Esters Under and Without Solvent Conditions

Decomposition Kinetics of 1,1-Dihydroperoxycyclohexane in Some Organic Solvents

In Silico Screening of Some Anti-Cancer Drugs Against the Main Protease of COVID-19 Using Molecular Docking