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A Lewis Acid-Catalyzed Diastereoselective Synthesis of Functionalized 2-Diazo-1,5-dicarbonyl Compounds
ACS Catalysis ( IF 11.3 ) Pub Date : 2021-09-16 , DOI: 10.1021/acscatal.1c03036 Evan M. Howard 1 , Matthias Brewer 1
ACS Catalysis ( IF 11.3 ) Pub Date : 2021-09-16 , DOI: 10.1021/acscatal.1c03036 Evan M. Howard 1 , Matthias Brewer 1
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A diverse array of 2-diazo-1,5-dicarbonyl compounds were formed by the Lewis acid-catalyzed reaction of enoxysilanes with β-hydroxy-α-diazo carbonyls. This reaction proceeds via the Zn(OTf)2-catalyzed dehydroxylation of the β-hydroxy-α-diazo carbonyl to form a vinyl diazonium ion intermediate that is intercepted by the enoxysilane nucleophile to give diazo-containing scaffolds with increased molecular complexity. The reaction appears to be general, and a variety of functional groups, including common protecting groups, are well tolerated. The 2-diazo-1,5-dicarbonyl products are formed in yields of up to 99% with diastereoselectivity up to >20:1.
中文翻译：
路易斯酸催化的功能化 2-重氮-1,5-二羰基化合物的非对映选择性合成
通过路易斯酸催化的烯氧基硅烷与 β-羟基-α-重氮羰基化合物的反应，形成了多种 2-重氮-1,5-二羰基化合物。该反应通过 Zn(OTf) 2催化的 β-羟基-α-重氮羰基脱羟基作用进行，形成乙烯基重氮离子中间体，该中间体被烯氧基硅烷亲核试剂截获，得到分子复杂性增加的含重氮支架。该反应似乎很普遍，并且可以很好地耐受各种官能团，包括常见的保护基团。2-重氮-1,5-二羰基产物的产率高达 99%，非对映选择性高达 >20:1。
更新日期：2021-10-01
中文翻译：
路易斯酸催化的功能化 2-重氮-1,5-二羰基化合物的非对映选择性合成
通过路易斯酸催化的烯氧基硅烷与 β-羟基-α-重氮羰基化合物的反应，形成了多种 2-重氮-1,5-二羰基化合物。该反应通过 Zn(OTf) 2催化的 β-羟基-α-重氮羰基脱羟基作用进行，形成乙烯基重氮离子中间体，该中间体被烯氧基硅烷亲核试剂截获，得到分子复杂性增加的含重氮支架。该反应似乎很普遍，并且可以很好地耐受各种官能团，包括常见的保护基团。2-重氮-1,5-二羰基产物的产率高达 99%，非对映选择性高达 >20:1。
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