Highly enantioselective access to syn-α,γ-dihydroxycarbonyl building blocks via organocatalyst-mediated aldol reaction as a key step

Yujiro Hayashi, Xiaoling Wang, Genki Kawauchi

Research output: Contribution to journalArticle

Abstract

An efficient synthesis of chiral syn-α,γ-dihydroxycarbonyl units from readily available achiral precursors in three pots under mild conditions was developed. This method explored the asymmetric direct cross-aldol reaction of two different aldehydes in the presence of an organocatalyst to generate a chiral βhydroxyaldehyde, which was converted into a 4-nitromethyl-1,3-dioxane derivative as a diastereo-mixture via a sequence of nitroalkane addition and acetalization. The 4-nitromethyl-1,3-dioxane derivative was then transformed either to a carboxylic ester or to an aldehyde/ketone. The chiral syn-α,γ-dialkoxy esters and aldehydes/ketones were all obtained with excellent enantiopurity and diastereoselectivity after a base-promoted epimerization.

Original languageEnglish
Pages (from-to)940-943
Number of pages4
JournalChemistry Letters
Volume49
Issue number8
DOIs
Publication statusPublished - 2020 Aug 5

Keywords

  • Asymmetric aldol reaction
  • Organocatalysis
  • Pot economy

ASJC Scopus subject areas

  • Chemistry(all)

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