Catalyst-Dependent Rate-Determining Steps in Regiodivergent Vinylogous Aza-Morita-Baylis-Hillman Reactions with N-Ts Imines

Naruhiro Gondo, Ryuichi Hyakutake, Koki Fujimura, Yoshihiro Ueda, Katsuhiko Nakano, Ryosuke Tsutsumi, Masahiro Yamanaka, Takeo Kawabata

Research output: Contribution to journalArticlepeer-review

Abstract

Catalyst-controlled vinylogous aza-MBH reactions of vinylcyclopentenone were performed, and it was found that the α-adducts were exclusively obtained by DABCO-catalysis, while the γ-adducts were the major products by DMAP-catalysis. We report here that the rate-determining step of the DABCO-catalyzed α-selective reactions is the Mannich-type C−C bond forming step, while that of the DMAP-catalyzed γ-selective reactions seems to be the β-elimination step.

Original languageEnglish
JournalAsian Journal of Organic Chemistry
DOIs
Publication statusAccepted/In press - 2021

Keywords

  • aza-Morita-Baylis-Hillman reaction
  • kinetic isotope effect
  • organocatalysis
  • rate-determining step
  • regioselectivity

ASJC Scopus subject areas

  • Organic Chemistry

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