Combining Palladium and Chiral Organocatalysis for the Enantioselective Deconjugative Allylation of Enals via Dienamine Intermediates

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Abstract

A catalytic enantioselective deconjugative allylation of enals is reported. A variety of enals underwent this transformation in high yield and ee, and products can be readily transformed into γ-allyl enals via a Cope rearrangement without erosion of ee. This transformation was used to install the quaternary stereocenter in (S)-bakuchiol, enabling completion of a concise formal synthesis.

Original languageEnglish (US)
Pages (from-to)866-873
Number of pages8
JournalJournal of Organic Chemistry
Volume87
Issue number1
DOIs
StatePublished - Jan 7 2022
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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