受阻异腈与受阻烷基硫代酸的偶联反应：机理研究。
Coupling reactions of hindered isonitriles and hindered alkyl thioacids: Mechanistic studies.
作者信息
Stockdill Jennifer L, Wu Xiangyang, Danishefsky Samuel J
机构信息
Laboratory for Bioorganic Chemistry, Sloan-Kettering Institute for Cancer Research, 1275 York Avenue, New York, NY 10065, USA.
出版信息
Tetrahedron Lett. 2009 Sep 9;50(36):5152-5155. doi: 10.1016/j.tetlet.2009.06.129.
Abstract
The coupling reaction between hindered thioacids and isonitriles is developed and described. The mechanism for the formation of the thiopyruvamide products is explored, and the method is applied to a selection of substrates.
摘要
受阻硫代酸与异腈之间的偶联反应得以开发并进行了描述。对硫代丙酮酰胺产物的形成机制进行了探索，并将该方法应用于一系列底物。
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1
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2
Noncatalytic reaction of isonitriles and carboxylic acids en route to amide-type linkages.
Nat Protoc. 2008;3(10):1666-70. doi: 10.1038/nprot.2008.153.
3
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J Am Chem Soc. 2008 Oct 8;130(40):13225-7. doi: 10.1021/ja804709s. Epub 2008 Sep 11.
4
On the two-component microwave-mediated reaction of isonitriles with carboxylic acids: regarding alleged formimidate carboxylate mixed anhydrides.
J Am Chem Soc. 2008 Oct 8;130(40):13222-4. doi: 10.1021/ja8047078. Epub 2008 Sep 11.
5
The coupling of isonitriles and carboxylic acids occurring by sequential concerted rearrangement mechanisms.
Org Lett. 2008 Sep 18;10(18):4093-6. doi: 10.1021/ol8016287. Epub 2008 Aug 16.
6
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J Am Chem Soc. 2008 Sep 10;130(36):11850-1. doi: 10.1021/ja803854r. Epub 2008 Aug 13.
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