迈向反应性的交响曲：涉及催化和σ迁移重排的级联反应。
Toward a symphony of reactivity: cascades involving catalysis and sigmatropic rearrangements.
作者信息
Jones Amanda C, May Jeremy A, Sarpong Richmond, Stoltz Brian M
出版信息
Angew Chem Int Ed Engl. 2014 Mar 3;53(10):2556-91. doi: 10.1002/anie.201302572.
Abstract
Catalysis and synthesis are intimately linked in modern organic chemistry. The synthesis of complex molecules is an ever evolving area of science. In many regards, the inherent beauty associated with a synthetic sequence can be linked to a certain combination of the creativity with which a sequence is designed and the overall efficiency with which the ultimate process is performed. In synthesis, as in other endeavors, beauty is very much in the eyes of the beholder. It is with this in mind that we will attempt to review an area of synthesis that has fascinated us and that we find extraordinarily beautiful, namely the combination of catalysis and sigmatropic rearrangements in consecutive and cascade sequences.
摘要
在现代有机化学中，催化与合成紧密相连。复杂分子的合成是一个不断发展的科学领域。在许多方面，与一个合成序列相关的内在美可以与序列设计的创造力和最终过程执行的整体效率的某种组合联系起来。在合成中，如同在其他领域一样，美很大程度上取决于旁观者的眼光。正是出于这个考虑，我们将尝试回顾一个令我们着迷且我们认为极其美妙的合成领域，即催化与连续和串联序列中的σ迁移重排的结合。
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本文引用的文献
1
"Biomimetic" Cascade Reactions in Organic Synthesis: Construction of 4-Oxatricyclo[4.3.1.0]decan-2-one Systems and Total Synthesis of 1-O-Methylforbesione via Tandem Claisen Rearrangement/Diels-Alder Reactions.有机合成中的“仿生”级联反应：通过串联克莱森重排/狄尔斯-阿尔德反应构建4-氧杂三环[4.3.1.0]癸烷-2-酮体系及1-O-甲基福布斯酮的全合成
Angew Chem Int Ed Engl. 2001 Nov 19;40(22):4264-4268. doi: 10.1002/1521-3773(20011119)40:22<4264::AID-ANIE4264>3.0.CO;2-1.
2
Catalytic enantioselective allylic amination of unactivated terminal olefins via an ene reaction/[2,3]-rearrangement.通过烯反应/[2,3]-重排实现非活化末端烯烃的催化对映选择性烯丙基胺化。
J Am Chem Soc. 2012 Nov 14;134(45):18495-8. doi: 10.1021/ja307851b. Epub 2012 Oct 29.
3
Rhodium-catalyzed acyloxy migration of propargylic esters in cycloadditions, inspiration from the recent "gold rush".铑催化炔丙酯在环加成反应中的酰氧基迁移，受近期“淘金热”的启发。
Chem Soc Rev. 2012 Dec 7;41(23):7698-711. doi: 10.1039/c2cs35235d.
4
A gold-catalysed enantioselective Cope rearrangement of achiral 1,5-dienes.金催化的外消旋 1,5-二烯的对映选择性 Cope 重排反应。
Nat Chem. 2012 Apr 15;4(5):405-9. doi: 10.1038/nchem.1327.
5
Generation and rearrangements of oxonium ylides.氧鎓叶立德的生成与重排。
J Am Chem Soc. 1986 Sep 1;108(19):6062-3. doi: 10.1021/ja00279a077.
6
Intramolecular generation and [2,3]-sigmatropic rearrangement of oxonium ylides.氧鎓叶立德的分子内生成及[2,3] - 迁移重排
J Am Chem Soc. 1986 Sep 1;108(19):6060-2. doi: 10.1021/ja00279a076.
7
Tandem catalytic allylic amination and [2,3]-Stevens rearrangement of tertiary amines.三级胺的串联催化烯丙基胺化和[2,3]-史蒂文斯重排反应。
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8
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Org Lett. 2010 Sep 3;12(17):3906-9. doi: 10.1021/ol101606v.
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