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Brønsted Acid-Initiated Formal [1,3]-Rearrangement Dictated by β-Substituted Ene-Aldimines

Author:
Jongwohan, Chanantida, Honda, Yasushi, Suzuki, Toshiyasu, Fujinami, Takeshi, Adachi, Kiyohiro, Momiyama, Norie
Source:
Organic letters 2019 v.21 no.13 pp. 4991-4995
ISSN:
1523-7052
Subject:
amines, cations, chemical reactions, chemical structure
Abstract:
The rearrangement of ene-aldimines is a useful reaction for affording homoallylic amines. Despite their utilities in synthetic chemistry, the rearrangement for accessing homoallylic amines substituted at the 2-position remains elusive. In this study, the Brønsted acid-initiated formal [1,3]-rearrangement of ene-aldimines was developed to synthesize 2,4,4-substituted homoallylic amines that were otherwise inaccessible previously. Our study reveals an intermolecular pathway in which the rearrangement proceeds via a protonation-mediated 2-azaallenium cation.
Agid:
6496882