Controllable Stereoselective Synthesis of (Z)- and (E)-Homoallylic Alcohols Using a Palladium-Catalyzed Three-Component Reaction

Yoshikazu Horino, Miki Sugata, Itaru Mutsuura, Keisuke Tomohara, Hitoshi Abe

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Diastereoselective synthesis of (Z)- and (E)-homoallylic alcohols using a Pd-catalyzed three-component reaction of 3-(pinacolatoboryl)allyl benzoates, aldehydes, and aryl stannanes was developed, which provides an alternative method for the allylboration of aldehydes using α, γ-diaryl-substituted allylboronates. Both sets of reaction conditions enable access to either (Z)- or (E)-homoallylic alcohols with good to high alkene stereocontrol. The present method showed good functional group compatibility and generality. Efficient chirality transfer reactions to afford enantioenriched (Z)- and (E)-homoallylic alcohols were also achieved.

Original languageEnglish
Pages (from-to)5968-5971
Number of pages4
JournalOrganic Letters
Volume19
Issue number21
DOIs
Publication statusPublished - Nov 3 2017
Externally publishedYes

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Palladium
palladium
alcohols
Alcohols
aldehydes
Aldehydes
synthesis
Acrolein
Chirality
Benzoates
Alkenes
chirality
compatibility
Functional groups
alkenes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Controllable Stereoselective Synthesis of (Z)- and (E)-Homoallylic Alcohols Using a Palladium-Catalyzed Three-Component Reaction. / Horino, Yoshikazu; Sugata, Miki; Mutsuura, Itaru; Tomohara, Keisuke; Abe, Hitoshi.

In: Organic Letters, Vol. 19, No. 21, 03.11.2017, p. 5968-5971.

Research output: Contribution to journalArticle

Horino, Yoshikazu ; Sugata, Miki ; Mutsuura, Itaru ; Tomohara, Keisuke ; Abe, Hitoshi. / Controllable Stereoselective Synthesis of (Z)- and (E)-Homoallylic Alcohols Using a Palladium-Catalyzed Three-Component Reaction. In: Organic Letters. 2017 ; Vol. 19, No. 21. pp. 5968-5971.
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