Aminocatalytic stereoselective synthesis of (E)-α-naphthyl enals via cross-coupling-like reaction of 1-bromo-2-naphthols with enals

Xixi Song, Fangchen Song, Xiang Meng, Peng Ji, Wei Wang

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

A diphenyl prolinol TMS ether-catalyzed stereoselective reaction of 1-bromo-2-naphthols with enals has been developed. The organocatalyzed cross coupling-like reaction servers an efficient approach to sterically congested (E)-α-naphthyl enals. The formal C(sp2)-C(sp2) cross-coupling products are obtained in good yields and with excellent stereoselectivities in favor of E-isomers. A broad range of aromatic enals and 1-bromo-2-naphthols are tolerated. The synthetic strategy significantly expands the scope of the organocatalytic cross-coupling-like reactions by enabling sterically demanding 1-bromo-2-naphthols as viable substrates.

Original languageEnglish (US)
Pages (from-to)377-380
Number of pages4
JournalGreen Synthesis and Catalysis
Volume2
Issue number4
DOIs
StatePublished - Nov 2021
Externally publishedYes

Keywords

  • Aminocatalysis
  • Cascade reaction
  • Cross coupling
  • Enal
  • Naphthol

ASJC Scopus subject areas

  • Biotechnology
  • Catalysis

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