Catalytic Conversion of Diazocarbonyl Compounds to Imines: Applications to the Synthesis of Tetrahydropyrimidines and beta-Lactams

The synthesis of alpha-carbonylimines by rhodium(II)-catalyzed reactions of alpha-diazoesters and organic azides has been developed and applied in hetero-Diels-Alder reactions to form highly functionalized tetrahydropyrimidines and in a one-pot, multicomponent transformation between aryldiazoacetate...

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Bibliographic Details
Published inOrganic letters Vol. 16; no. 3; pp. 740 - 743
Main Authors Mandler, Michael D., Truong, Phong M., Zavalij, Peter Y., Doyle, Michael P.
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 07.02.2014
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
AMINATION
KETENES
DIELS-ALDER REACTIONS
MECHANISM
IMIDOMETAL COMPLEXES
CHEMISTRY
INTERMEDIATE
ORGANIC AZIDES
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Summary:The synthesis of alpha-carbonylimines by rhodium(II)-catalyzed reactions of alpha-diazoesters and organic azides has been developed and applied in hetero-Diels-Alder reactions to form highly functionalized tetrahydropyrimidines and in a one-pot, multicomponent transformation between aryldiazoacetates, p-anisyl azide, and an enonediazoacetate to produce beta-lactams in high yields and diastereoselectivities.
Bibliography:National Science Foundation
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol403427s