Enantioselective protonation/diastereoselective reduction with sodium naphthalenide-acetamide; a new synthesis of chiral trans-2-phenylcyclohexanol

Gregorio Asensio*, A. Cuenca, P. Gaviña, Mercedes Medio-Simón

*Corresponding author for this work

Research output: Indexed journal article Articlepeer-review

21 Citations (Scopus)

Abstract

An efficient synthesis of trans-2-phenylcyclohexanol has been achieved by enantioselective protonation of the enolate of 2-phenylcyclohexanone with α-sulfinyl alcohols and subsequent reduction of the chiral ketone by sodium naphthalenide in the presence of acetamide. Interestingly, the chirality source is not consumed in the synthesis of the chiral target.

Original languageEnglish
Pages (from-to)3939-3940
Number of pages2
JournalTetrahedron Letters
Volume40
Issue number20
DOIs
Publication statusPublished - 14 May 1999
Externally publishedYes

Keywords

  • Alpha-sulfinyl alcohols
  • Protonation
  • Alkylation

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