"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 journalArticle

91 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

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Cycloaddition
Cycloaddition Reaction
cycloaddition
Alkenes
alkenes
Ions
ions
Alkynes
alkynes
Discrete Fourier transforms
Cations
cations
matrices

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

"N-acyliminium ion pool" as a heterodiene in [4 + 2] cycloaddition reaction. / Suga, Seiji; Nagaki, Aiichiro; Tsutsui, Yamato; Yoshida, Jun Ichi.

In: Organic Letters, Vol. 5, No. 6, 20.03.2003, p. 945-947.

Research output: Contribution to journalArticle

Suga, Seiji ; Nagaki, Aiichiro ; Tsutsui, Yamato ; Yoshida, Jun Ichi. / "N-acyliminium ion pool" as a heterodiene in [4 + 2] cycloaddition reaction. In: Organic Letters. 2003 ; Vol. 5, No. 6. pp. 945-947.
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