Catalytic Asymmetric Synthesis of α-Trifluoromethylated Carbinols: A Case Study of Tertiary Propargylic Alcohols

Hidetoshi Noda, Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journalReview articlepeer-review

18 Citations (Scopus)

Abstract

Enantioenriched CF3-substituted tertiary alcohols have been applied in a broad range of chemical disciplines, including medicinal chemistry and agrochemistry. The widely prescribed anti-HIV pharmaceutical efavirenz is one particular example of the application of these chiral building blocks. Because the typical synthetic route to this small drug molecule involves the stoichiometric use of a chiral promoter, significant effort has been devoted to the development of catalytic alternatives for accessing this building block. In this Focus Review, we summarize the catalytic asymmetric synthesis of CF3-substituted tertiary propargylic alcohols based on three retrosynthetic approaches, namely one trifluoromethylation approach and two building-block strategies. The general challenges that are involved in the construction of a CF3-substituted tetrasubstituted stereogenic carbon species are highlighted and possible future directions in the field are discussed.

Original languageEnglish
Pages (from-to)599-612
Number of pages14
JournalAsian Journal of Organic Chemistry
Volume7
Issue number4
DOIs
Publication statusPublished - 2018 Apr
Externally publishedYes

Keywords

  • alcohols
  • alkynes
  • asymmetric catalysis
  • fluorine
  • synthetic methods

ASJC Scopus subject areas

  • Organic Chemistry

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