Vicinal difunctionalization of dehydropiperidines using α-chloro-β-sulfonyl eneformamides

[Display omitted] The synthesis of α,β-difunctionalized dehydropiperidines has been accomplished using α-halo-β-sulfonyl eneformamides. This outcome is achieved through sequential regioselective Cβ-alkylative desulfonation and Cα-palladium-catalyzed cross-coupling. In most cases, high yields of the...

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Bibliographic Details
Published inTetrahedron letters Vol. 55; no. 49; pp. 6662 - 6664
Main Authors Beng, Timothy K., Bassler, Daniel P.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 03.12.2014
Elsevier
Subjects
Alkylative desulfonation
Chemistry
Chemistry, Organic
Cross coupling
Physical Sciences
Piperidine alkaloids
Science & Technology
Synthesis
Tetrahedrons
Vicinal difunctionalization
α-Halo eneformamides
β-Sulfonyl eneformamides
β-Sulfonyl eneformamides
Alkylative desulfonation
Cross-coupling
Piperidine alkaloids
α-Halo eneformamides
Vicinal difunctionalization
INDOLIZIDINE
SALTS
alpha-Halo eneformamides
beta-Sulfonyl eneformamides
CATALYTIC DYNAMIC RESOLUTION
STEREOCONTROLLED ALKYLATION
CYCLIC ENAMINONES
STEREOSELECTIVE-SYNTHESIS
PIPERIDINES
GRIGNARD-REAGENTS
ACID-DERIVED ENAMINONES
ALKALOIDS
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Summary:[Display omitted] The synthesis of α,β-difunctionalized dehydropiperidines has been accomplished using α-halo-β-sulfonyl eneformamides. This outcome is achieved through sequential regioselective Cβ-alkylative desulfonation and Cα-palladium-catalyzed cross-coupling. In most cases, high yields of the vicinally functionalized eneformamides are obtained.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2014.10.063