Carbon–carbon bond formation via a tandem cationic 2-aza-Cope rearrangement–Lewis acid promoted Petasis reaction

Potassium alkynyltrifluoroborates and potassium (2-phenyl)vinyltrifluoroborates react with N-3-butenyl-(2,2-dichloro-1-propylidene)amine in the presence of BF 3·Et 2O as a Lewis acid to synthesize rearranged Mannich products. The reaction starts with a cationic 2-aza-Cope rearrangement of the imine,...

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Bibliographic Details
Published inTetrahedron Vol. 64; no. 16; pp. 3457 - 3463
Main Authors Stas, Sara, Abbaspour Tehrani, Kourosch, Laus, Georges
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 14.04.2008
Elsevier
Subjects
2-Aza-Cope
Boron
Chemistry
Chemistry, Organic
Imine
Petasis
Physical Sciences
Science & Technology
Tandem reaction
Boron
Imine
Tandem reaction
2-Aza-Cope
Petasis
tandem reaction
ASYMMETRIC-SYNTHESIS
imine
ALPHA-AMINO-ACIDS
2-aza-Cope
STEREOSELECTIVE SYNTHESIS
AZA-COPE REARRANGEMENTS
FACILE SYNTHESIS
STEREOCONTROLLED TOTAL-SYNTHESIS
3-AZA-COPE REARRANGEMENT
GENERATION
boron
MANNICH CYCLIZATIONS
STRYCHNOS ALKALOIDS
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Summary:Potassium alkynyltrifluoroborates and potassium (2-phenyl)vinyltrifluoroborates react with N-3-butenyl-(2,2-dichloro-1-propylidene)amine in the presence of BF 3·Et 2O as a Lewis acid to synthesize rearranged Mannich products. The reaction starts with a cationic 2-aza-Cope rearrangement of the imine, followed by the Lewis acid promoted borono-Mannich-type reaction on the rearranged imine to result in a new class of functionalized N-homoallylamines. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2008.02.025