Gold-catalyzed synthesis of polycyclic enones from carbon tethered 1,3-enynyl carbonyls via tandem heteroenyne metathesis and Nazarov reaction

Gold-catalyzed synthesis of polycyclic enones from carbon tethered 1,3-enynyl carbonyls via tandem heteroenyne metathesis and Nazarov reaction
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DOI:
10.1021/ol801265s
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发表时间:
2008-07-17
期刊:
影响因子:
5.2
通讯作者:
Yamamoto, Yoshinori
Yamamoto, Yoshinori
中科院分区:
化学1区
文献类型:
--
作者:
Jin, Tienan;Yamamoto, Yoshinori

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研究了一种高效、通用的金(III)催化1,3-乙烯基酮的杂炔复合和Nazarov环化串联反应,以合成三环和四环烯酮。产物对双键位置具有良好的区域选择性和非常高的非对映选择性。在该反应中,Au(III)催化剂表现出活化炔烃和羰基的双重作用。
An efficient and general Au(III)-catalyzed tandem reaction, heteroenyne metathesis and Nazarov cyclization, of 1,3-enynyl ketones to produce fused tri- and tetracyclic enones has been developed. The products were formed with excellent regioselectivity of the double bond position and with very high diastereoselectivities. In this reaction, the Au(III) catalyst exhibits dual roles for activating both alkynes and carbonyls.