Synthesis of Highly Stereodefined Tetrasubstituted Acyclic All-Carbon Olefins via a Syn-Elimination Approach,Organic Letters

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Synthesis of Highly Stereodefined Tetrasubstituted Acyclic All-Carbon Olefins via a Syn-Elimination Approach
Organic Letters ( IF 4.9 ) Pub Date : 2017-11-08 00:00:00 , DOI: 10.1021/acs.orglett.7b03141
Ngiap-Kie Lim ₁ , Patrick Weiss ₁ , Beryl X. Li ₁ , Christina H. McCulley ₂ , Stephanie R. Hare ₂ , Bronwyn L. Bensema ₂ , Teresa A. Palazzo ₂ , Dean J. Tantillo ₂ , Haiming Zhang ₁ , Francis Gosselin ₁

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An efficient synthesis of stereodefined tetrasubstituted acyclic all-carbon olefins has been developed via a bis(2,6-xylyl)phosphate formation of stereoenriched tertiary alcohols, followed by in situ syn-elimination of the corresponding phosphates under mild conditions. This chemistry tolerates a wide variety of electronically and sterically diverse substrates and generates the desired tetrasubstituted olefins in high yields and stereoselectivities (>95:5) in most cases. This stereocontrolled olefin synthesis has been applied to the synthesis of anticancer drug tamoxifen in three steps from commercially available 1,2-diphenylbutan-1-one in 97:3 stereoselectivity and 78% overall yield.

中文翻译：

通过高度Stereodefined四取代非周期性全碳烯烃合成的Syn在剔除方法

通过形成双（2,6-二甲苯基）磷酸形成富含立体异构的叔醇，然后在温和条件下原位合成消除相应的磷酸酯，已经开发出有效合成立体确定的四取代的无环全碳烯烃的方法。在大多数情况下，这种化学方法可耐受多种电子和空间上不同的底物，并以高收率和立体选择性（> 95：5）生成所需的四取代烯烃。该立体控制的烯烃合成已经以三步法从97：3立体选择性和78％的总收率应用到抗癌药他莫昔芬的合成中，该步骤由市售的1,2-二苯基丁烷-1-酮合成。

更新日期：2017-11-08

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