Palladium-Catalyzed 1,4-Difunctionalization of Butadiene To Form Skipped Polyenes

被引：138
|
作者：
McCammant, Matthew S. [1 ]
Liao, Longyan [1 ]
Sigman, Matthew S. [1 ]
机构：
[1] Univ Utah, Dept Chem, Salt Lake City, UT 84112 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2013年 / 135卷 / 11期
基金：
美国国家卫生研究院;
关键词：
CONJUGATED DIENES; MARINE SPONGE; PD(0)-CATALYZED DIAMINATION; STEREOCHEMICAL ASSIGNMENT; STEREOSPECIFIC SYNTHESIS; STRUCTURE ELUCIDATION; COUPLING REACTIONS; INTERNAL ALKYNES; TERMINAL ALKENES; INHIBITOR;
D O I：
10.1021/ja3110544
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A palladium-catalyzed 1,4-addition across the commodity chemical 1,3-butadiene to afford skipped polyene products is reported. Through a palladium sigma -> pi -> sigma allyl isomerization, two new carbon-carbon bonds are formed with high regioselectivity and trans stereoselectivity of the newly formed alkene. The utility of this method is highlighted by the successful synthesis of the ripostatin A skipped triene core.
引用
收藏
页码：4167 / 4170
页数：4
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