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

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

doi:10.1021/ol0341243

"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 journal › Article › peer-review

103 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 language	English
Pages (from-to)	945-947
Number of pages	3
Journal	Organic Letters
Volume	5
Issue number	6
DOIs	https://doi.org/10.1021/ol0341243
Publication status	Published - Mar 20 2003
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol0341243

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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.",

author = "Seiji Suga and Aiichiro Nagaki and Yamato Tsutsui and Yoshida, {Jun Ichi}",

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doi = "10.1021/ol0341243",

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journal = "Organic Letters",

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T1 - "N-acyliminium ion pool" as a heterodiene in [4 + 2] cycloaddition reaction

AU - Suga, Seiji

AU - Nagaki, Aiichiro

AU - Tsutsui, Yamato

AU - Yoshida, Jun Ichi

PY - 2003/3/20

Y1 - 2003/3/20

N2 - (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.

AB - (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.

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JO - Organic Letters

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

Abstract

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