Organocatalyzed Enantioselective [2 + 2] Cycloaddition of C,N-Cyclic Ketimines and Allenoates

Xinyu Liu, Fangfang Zhu, Manjaly J. Ajitha, Yunfeng Zhang, Kuo Wei Huang*, Dehai Li*, De Wang*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

We report a novel enantioselective and regioselective [2 + 2] cycloaddition of allenoate and C,N-cyclic ketimine catalyzed by a quinidine derivative. The methodology enables the synthesis of fused tricyclic azetidines with a quaternary stereogenic center exhibiting high enantioselectivities. The broad range of substrates demonstrates the generality of the protocol, and the resulting functional products can be easily converted to a variety of valuable synthons. To elucidate the plausible reaction mechanism and how the catalyst affects absolute stereocontrol over the products, we conducted the corresponding density functional theory (DFT) calculations.

Original languageEnglish (US)
Pages (from-to)225-230
Number of pages6
JournalOrganic Letters
Volume26
Issue number1
DOIs
StatePublished - Jan 12 2024

Bibliographical note

Publisher Copyright:
© 2023 American Chemical Society.

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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