"N-acyliminium ion pool" as a heterodiene in [4 + 2] cycloaddition reaction.
[reaction: see text] 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.
Suga
Seiji
S
Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 606-8501, Japan. suga@sbchem.kyoto-u.ac.jp
Nagaki
Aiichiro
A
Tsutsui
Yamato
Y
Yoshida
Jun-Ichi
J