"N-acyliminium ion pool" as a heterodiene in [4 + 2] cycloaddition reaction

Seiji Suga, Aiichiro Nagaki, Yamato Tsutsui, Jun Ichi Yoshida

Research output: Contribution to journalArticlepeer-review

94 Citations (Scopus)

Abstract

(Matrix presented). An N-acyliminium ion pool was found to undergo cycloaddition reaction with a variety of dienophiles such as alkenes and alkynes. A concerted mechanism seems to be most likely for alkyl-substituted alkenes as suggested by the DFT calculations, whereas a stepwise mechanism plays the major role for aryl-substituted alkenes. It is also noteworthy that the present study demonstrates the potential of the combination of the cation pool method and the micromixing in both mechanistic and synthetic aspects.

Original languageEnglish
Pages (from-to)945-947
Number of pages3
JournalOrganic Letters
Volume5
Issue number6
DOIs
Publication statusPublished - Mar 20 2003
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint Dive into the research topics of '"N-acyliminium ion pool" as a heterodiene in [4 + 2] cycloaddition reaction'. Together they form a unique fingerprint.

Cite this