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

研究成果: Article査読

抄録

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.

本文言語English
ページ(範囲)161-174
ページ数14
ジャーナルSynthesis (Germany)
53
1
DOI
出版ステータスPublished - 2021 1 5
外部発表はい

ASJC Scopus subject areas

  • 触媒
  • 有機化学

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