Construction of Highly Substituted Stereodefined Dienes by Cross‐Coupling of α‐Allenic Acetates
Construction of Highly Substituted Stereodefined Dienes by Cross‐Coupling of α‐Allenic Acetates
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通过α-烯乙酸酯交叉偶联构建高度取代的立体二烯
DOI：
10.1002/ejoc.200600721
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发表时间：
2007
影响因子：
2.8
通讯作者：
C. Crews
中科院分区：
文献类型：
--
作者：
J. Schneekloth;Mathieu Pucheault;C. Crews
高取代二烯的组装仍然是有机化学的一个挑战。本研究提出了一种通过α-丙烯酸酯和有机锌试剂之间的Tsuji-Trost交叉偶联构建高取代的1,3-二烯的策略。该反应产率高，并安装了三取代烯烃，E/Z选择性高达95:5，有利于(E)产物。一种廉价的、市售的钯预催化剂和配体用于控制theE/Z选择性。此外，注意到选择性的有趣逆转，其中适当的配体选择可以用来控制反应的结果并有利于(Z)产物。描述了13个例子，突出了反应的底物范围。该反应具有简单的反应条件和高选择性，有望在天然产物化学中得到广泛应用。（©Wiley-VCH Verlag GmbH & Co. KGaA，德国Weinheim 69451, 2007）
The assembly of highly substituted dienes remains a challenge for organic chemistry. This work represents a strategyfor the construction of highly substituted 1,3-dienes by meansof a Tsuji–Trost cross coupling between α-allenic acetates and organozinc reagents. The reaction is high yielding, and installs a trisubstituted olefin with E/Z selectivities up to 95:5 favoring the (E) product. A cheap, commercially available palladium precatalyst and a ligand are used to control theE/Z selectivity. Furthermore, an interesting reversal in selectivity is noted in which appropriate choice of ligand may be used to control the outcome of the reaction and favor the (Z) product. Thirteen examples are described, highlighting the substrate scope of the reaction. It is hoped that the straightforward reaction conditions and high selectivity will make this reaction of broad use in natural product chemistry. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
通过联二烯乙酸酯和 (B)-烷基硼烷之间的偶联立体选择性组装 1,3-二烯：amphidinolide B1 的合成研究。
影响因子：
5.2
作者：
Mandal,AmitK;SchneeklothJr,JohnS;Crews,CraigM
通讯作者：
Crews,CraigM