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

• Published in: Tetrahedron Vol. 64; no. 16; pp. 3457 - 3463
• Main Authors: Stas, Sara, Abbaspour Tehrani, Kourosch, Laus, Georges
• Format: Journal Article
• Language: English
• 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

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,...