Stereodivergent Carbon-Carbon Bond Formation between Iminium and Enolate Intermediates by Synergistic Organocatalysis

Byungjun Kim, Yongjae Kim, Sarah Yunmi Lee

Research output: Contribution to journalArticlepeer-review

43 Citations (Scopus)


We report here a stereodivergent method for the Michael addition of aryl acetic acid esters to α,β-unsaturated aldehydes catalyzed by a combination of a chiral pyrrolidine and a chiral Lewis base. This reaction proceeds through a synergistic catalytic cycle which consists of one cycle leading to a chiral iminium electrophile and a second cycle generating a nucleophilic chiral enolate for the construction of a carbon-carbon bond. By varying the combinations of catalyst enantiomers, all four stereoisomers of the products with two vicinal stereocenters are accessible with high enantio- and diastereoselectivity. The products of the Michael addition, 1,5-aldehyde esters, can be readily transformed into a variety of other valuable enantioenriched structures, including those bearing three contiguous stereocenters in an acyclic system, thus providing an efficient route to an array of structural and stereochemical diversity.

Original languageEnglish
Pages (from-to)73-79
Number of pages7
JournalJournal of the American Chemical Society
Issue number1
Publication statusPublished - 2021 Jan 13

Bibliographical note

Funding Information:
This work was supported by 1) the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Science, ICT & Future Planning (2018R1C1B6005712), 2) the Yonsei University Future-leading Research Initiative of 2018 (22-0055), and 3) the POSCO Cheongam Foundation (Fellowship to S.Y.L.). We thank Yuna Song for assistance. S.Y.L. thanks Dr. Taegyo Lee (Pfizer) for helpful discussions.

Publisher Copyright:
© 2020 American Chemical Society.

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry


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