2021年1月5日
Stereoselective 1,4-Addition of Primary Alcohols to γ-Alkoxy-α,β-unsaturated Esters
Synthesis (Germany)
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- 巻
- 53
- 号
- 1
- 開始ページ
- 161
- 終了ページ
- 174
- 記述言語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.1055/s-0040-1707274
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 Cl at -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. 2 2
- リンク情報
- ID情報
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- DOI : 10.1055/s-0040-1707274
- ISSN : 0039-7881
- eISSN : 1437-210X
- SCOPUS ID : 85091743744