Highly Regio- and Stereoselective Catalytic Synthesis of Conjugated Dienes and Polyenes.

Highly Regio- and Stereoselective Catalytic Synthesis of Conjugated Dienes and Polyenes.
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DOI:
10.1021/jacs.8b05421
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发表时间:
2018-07-11
影响因子:
15
通讯作者:
Larionov OV
Larionov OV
中科院分区:
化学1区
文献类型:
--
作者:
Nguyen VT;Dang HT;Pham HH;Nguyen VD;Flores-Hansen C;Arman HD;Larionov OV

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共轭二烯和多烯通常通过连续引入C=C键来合成。在这里,我们报告了一个实用的和可扩展的,催化二烯化,是高度区域和立体选择性的两个C=C键。该反应通过立体选择性钯催化的交叉偶联实现,该偶联之前是容易获得的环丁砜的区域选择性碱诱导的开环。二烯基化反应对于合成具有挑战性的含有顺式双键的二烯的合成特别有用。我们还表明,该反应可以作为一个合成平台的共轭多烯的建设。
Conjugated dienes and polyenes are typically synthesized by sequential introduction of C=C bonds. Here, we report a practical and scalable, catalytic dienylation that is highly regio- and stereoselective for both C=C bonds. The reaction is enabled by a stereoselective palladium-catalyzed cross-coupling that is preceded by a regioselective base-induced ring opening of readily available sulfolenes. The dienylation reaction is particularly useful for the synthesis of synthetically challenging dienes containing cis double bonds. We also show that the reaction can serve as a synthetic platform for the construction of conjugated polyenes.
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