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Z-α-芳基-α,β-不饱和酯的立体选择性合成

Stereoselective synthesis of Z-alpha-aryl-alpha,beta-unsaturated esters.

作者信息

Mani Neelakandha S, Mapes Christopher M, Wu Jiejun, Deng Xiaohu, Jones Todd K

机构信息

Department of Drug Discovery, Johnson & Johnson Pharmaceutical Research and Development, L.L.C., 3210 Merryfield Row, San Diego, California 92121, USA.

出版信息

J Org Chem. 2006 Jun 23;71(13):5039-42. doi: 10.1021/jo060586t.

DOI:10.1021/jo060586t
PMID:16776544
Abstract

An efficient method for the stereoselective synthesis of (Z)-alpha-arylacrylates is described. Treatment of alpha-hydroxyesters with triflic anhydride and pyridine at 0 degrees C followed by warming to room temperature afforded the corresponding (Z)-alpha-aryl-alpha,beta-unsaturated esters in very good yields and excellent stereoselectivity.

摘要

描述了一种立体选择性合成(Z)-α-芳基丙烯酸酯的有效方法。α-羟基酯在0℃下用三氟甲磺酸酐和吡啶处理,然后升温至室温,以非常高的产率和优异的立体选择性得到相应的(Z)-α-芳基-α,β-不饱和酯。

相似文献

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Stereoselective synthesis of Z-alpha-aryl-alpha,beta-unsaturated esters.Z-α-芳基-α,β-不饱和酯的立体选择性合成
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Ethyl (benzothiazol-2-ylsulfonyl)acetate: a new reagent for the stereoselective synthesis of alpha,beta-unsaturated esters from aldehydes.(苯并噻唑 -2- 基磺酰基)乙酸乙酯:一种用于从醛立体选择性合成α,β - 不饱和酯的新试剂。
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Kinetic separation methodology for the stereoselective synthesis of (E)- and (Z)-alpha-fluoro-alpha,beta-unsaturated esters via the palladium-catalyzed carboalkoxylation of 1-bromo-1-fluoroalkenes.通过钯催化的1-溴-1-氟烯烃的碳烷氧基化反应立体选择性合成(E)-和(Z)-α-氟-α,β-不饱和酯的动力学分离方法。
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Highly stereoselective synthesis of (E)- and (Z)-alpha-fluoro-alpha,beta-unsaturated esters and (E)- and (Z)-alpha-fluoro-alpha,beta-unsaturated amides from 1-bromo-1-fluoroalkenes via palladium-catalyzed carbonylation reactions.通过钯催化的羰基化反应,从1-溴-1-氟烯烃高度立体选择性地合成(E)-和(Z)-α-氟-α,β-不饱和酯以及(E)-和(Z)-α-氟-α,β-不饱和酰胺。
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