Literature DB >> 18338857

Efficient synthesis of gamma-lactams by a tandem reductive amination/lactamization sequence.

Julica Nöth1, Kevin J Frankowski, Benjamin Neuenswander, Jeffrey Aubé, Oliver Reiser.   

Abstract

A three-component method for the synthesis of highly substituted gamma-lactams from readily available maleimides, aldehydes, and amines is described. A new reductive amination/intramolecular lactamization sequence provides a straightforward route to the lactam products in a single manipulation. The general utility of this method is demonstrated by the parallel synthesis of a gamma-lactam library.

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Year:  2008        PMID: 18338857      PMCID: PMC2713763          DOI: 10.1021/cc700202c

Source DB:  PubMed          Journal:  J Comb Chem        ISSN: 1520-4766


  22 in total

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6.  Diastereoselective synthesis of gamma-lactams by a one-pot, four-component reaction.

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9.  A novel synthetic route to chiral gamma-lactams from alpha-amino acids via Rh-catalyzed intramolecular C-H insertion.

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10.  Highly diastereoselective synthesis of beta-carboxy-gamma-lactams and their ethyl esters via Sc(OTf)(3)-catalyzed imino Mukaiyama-aldol type reaction of 2,5-bis(trimethylsilyloxy)furan with imines.

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  6 in total

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2.  A facile synthesis of 2-aryloxypyrimidine derivatives via a tandem reductive amination/intermolecular S(N)Ar sequence.

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4.  Asymmetric Conjugate Addition of Ketones to Maleimides Organocatalyzed by a Chiral Primary Amine-Salicylamide.

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5.  Automated three-component synthesis of a library of γ-lactams.

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6.  Organocatalytic Asymmetric Conjugate Addition of Aldehydes to Maleimides and Nitroalkenes in Deep Eutectic Solvents.

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  6 in total

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