Palladium/zinc co-catalyzed syn-stereoselectively asymmetric ring-opening reaction of oxabenzonorbornadienes with phenols

Sifeng Li, Jianbin Xu, Baomin Fan*, Zhiwu Lu, Chaoyuan Zeng, Zhaoxiang BIAN, Yongyun Zhou, Jun WANG

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

38 Citations (Scopus)

Abstract

A new palladium/zinc co-catalyst system associated with chiral (R)-Difluorphos for asymmetric ring-opening reaction of oxabenzonorbornadienes with phenols is reported. This catalyst system allows the formation of cis-2-aryloxy-1,2-dihydronaphthalen-1-ol products in good yields (up to 95-% yield) with excellent enantioselectivities (up to 99-% ee). The cis-configuration of the product has been confirmed by X-ray crystal structure analysis. To the best of our knowledge, it represents the first example in ring-opening reactions of bicycloalkenes with heteronucleophiles in a syn-stereoselective manner. Open the ring: A new palladium/zinc co-catalyst associated with chiral (R)-Difluorphos for asymmetric ring-opening reaction of oxabenzonorbornadienes with phenolic or naphtholic nucleophiles was developed, which afforded the corresponding cis-2-aryloxy-1,2-dihydronaphthalen-1-ol products in good yields (up to 95-% yield) with excellent enantioselectivities (up to 99-% ee).

Original languageEnglish
Pages (from-to)9003-9007
Number of pages5
JournalChemistry - A European Journal
Volume21
Issue number25
DOIs
Publication statusPublished - 1 Jun 2015

Scopus Subject Areas

  • Catalysis
  • Organic Chemistry

User-Defined Keywords

  • asymmetric catalysis
  • oxabenzonorbornadienes
  • phenols
  • ring-opening reaction
  • syn-stereoselectivity

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