Remote Stereocontrolled Construction of Vicinal Axially Chiral Tetrasubstituted Allenes and Heteroatom-Functionalized Quaternary Carbon Stereocenters

Pei Zhang, Qiuhong Huang, Yuyu Cheng, Rongshi Li, Pengfei Li, Wenjun Li

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

The direct diastereo- and enantioselective 1,8-conjugate additions of thiazolones and azlactones, respectively, to para-quinone methides generated in situ from propargylic alcohols have been achieved in the presence of chiral phosphoric acids. The remote stereocontrolled activation protocol provides an efficient and facile approach for the construction of vicinal axially chiral tetrasubstituted allenes and heteroatom-functionalized quaternary carbon stereocenters, which expands the synthetic potential of chiral phosphoric acids.

Original languageEnglish (US)
Pages (from-to)503-507
Number of pages5
JournalOrganic Letters
Volume21
Issue number2
DOIs
StatePublished - Jan 18 2019

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Phosphoric Acids
phosphoric acid
Carbon
carbon
quinones
alcohols
Chemical activation
Alcohols
activation
propadiene

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Remote Stereocontrolled Construction of Vicinal Axially Chiral Tetrasubstituted Allenes and Heteroatom-Functionalized Quaternary Carbon Stereocenters. / Zhang, Pei; Huang, Qiuhong; Cheng, Yuyu; Li, Rongshi; Li, Pengfei; Li, Wenjun.

In: Organic Letters, Vol. 21, No. 2, 18.01.2019, p. 503-507.

Research output: Contribution to journalArticle

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