Stereoselective 1,4-Addition of Primary Alcohols to γ-Alkoxy-α,β-unsaturated Esters

Saki Inatomi, Yuta Takayanagi, Kento Watanabe, Akinori Toita, Hiroyuki Yamakoshi, Seiichi Nakamura

Research output: Contribution to journalArticlepeer-review

Abstract

The scope and limitations of the diastereoselective 1,4-addition reaction of primary alcohols to γ-alkoxy-α,β-unsaturated esters were investigated. We found that a variety of sodium alkoxides, generated from the corresponding primary alcohols with NaH, underwent 1,4-addition reactions with (E)-enoates in CH 2Cl 2at -23 °C to give β-alkoxy esters in modest yields with good to excellent syn -selectivity, whereas stereoselectivity was not observed with the use of glycerol derivatives as nucleophiles. Cyclic acetal protection was found to play a pivotal role for the reaction to proceed.

Original languageEnglish
Pages (from-to)161-174
Number of pages14
JournalSynthesis (Germany)
Volume53
Issue number1
DOIs
Publication statusPublished - 2021 Jan 5
Externally publishedYes

Keywords

  • 1,4-addition
  • cyclic acetals
  • primary alcohols
  • syn -selectivity
  • γ-alkoxy-α,β-unsaturated esters

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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