Gold(I)-Catalyzed 1,6-Enyne Single-Cleavage Rearrangements: The Complete Picture

IF 3.3 Q2 CHEMISTRY, MULTIDISCIPLINARY ACS Organic & Inorganic Au Pub Date : 2023-08-20 DOI:10.1021/acsorginorgau.3c00028
Eduardo García-Padilla, Feliu Maseras* and Antonio M. Echavarren*, 
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Abstract

We identify the factors that rule the selectivity in single-cleavage skeletal rearrangements promoted by gold(I) catalysts. We find that stereoconvergence is enabled by a rotational equilibrium when electron-rich substituents are used. The anomalous Z-selective skeletal rearrangement is found to be due to electronic factors, whereas endo-selectivity depends on both steric and electronic factors.

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金(I)催化的1,6-Enyne单次裂解重排:全貌。
我们确定了在金(I)催化剂促进的单切割骨架重排中控制选择性的因素。我们发现,当使用富含电子的取代基时,立体会聚是通过旋转平衡实现的。发现异常的Z选择性骨架重排是由电子因素引起的,而内选择性则取决于空间和电子因素。
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ACS Organic & Inorganic Au
ACS Organic & Inorganic Au 有机化学、无机化学-
CiteScore
4.10
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0.00%
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期刊介绍: ACS Organic & Inorganic Au is an open access journal that publishes original experimental and theoretical/computational studies on organic organometallic inorganic crystal growth and engineering and organic process chemistry. Short letters comprehensive articles reviews and perspectives are welcome on topics that include:Organic chemistry Organometallic chemistry Inorganic Chemistry and Organic Process Chemistry.
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