Synthesis ( IF 2.2 ) Pub Date : 2020-09-22 , DOI: 10.1055/s-0040-1707274 Seiichi Nakamura , Saki Inatomi , Yuta Takayanagi , Kento Watanabe , Akinori Toita , Hiroyuki Yamakoshi 1
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 CH2Cl2 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.
Publication History
Received: 03 July 2020
Accepted after revision: 07 August 2020
Publication Date:
22 September 2020 (online)
© 2020. Thieme. All rights reserved
Georg Thieme Verlag KG
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中文翻译:
γ-烷氧基-α,β-不饱和酯对伯醇的立体选择性1,4-加成
摘要
研究了伯醇对γ-烷氧基-α,β-不饱和酯的非对映选择性1,4-加成反应的范围和局限性。我们发现,由相应的伯醇与NaH生成的各种烷醇钠,在–23°C下与CH 2 Cl 2中的(E)-烯酸酯进行1,4-加成反应,以中等收率得到β-烷氧基酯具有良好至优异的顺选择性,而使用甘油衍生物作为亲核试剂未观察到立体选择性。发现环缩醛保护对于反应的进行起关键作用。
出版历史
收到:2020年7月3日
修订后接受:2020年8月7日
发布日期:
2020年9月22日(在线)
©2020年。Thieme。版权所有
Georg Thieme Verlag
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