Cobalt Catalyzed Reductive Spirocyclopropanation Reactions

被引：19

作者：

Werth, Jacob ^{[1
]}

Berger, Kristen ^{[1
]}

Uyeda, Christopher ^{[1
]}

机构：

[1] Purdue Univ, Dept Chem, 560 Oval Dr, W Lafayette, IN 47907 USA

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2020年 / 362卷 / 02期

关键词：

cyclopropanes; spiro compounds; cobalt; carbenes; carbenoids; STEREOSELECTIVE-SYNTHESIS; HYDRAZONES; OXIDATION; CYCLOPROPANOLS; IODINE; ESTERS;

D O I：

10.1002/adsc.201901293

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Cobalt pyridine-diimine (PDI) complexes catalyze the reductive spirocyclopropanation of terminal 1,3-dienes. gem-Dichlorocycloalkanes serve as carbene precursors and Zn is used as a terminal electron source. The reaction is effective for a range of gem-dichloro partners including those containing sulfur and nitrogen heterocycles. An example of an intramolecular Rh-catalyzed [5+2]-cycloaddition of a vinyl spirocyclopropane is demonstrated, providing rapid access to a complex tricyclic framework. Overall, this catalyst system is capable of suppressing the kinetically facile 1,2-hydride shift, which has hampered the development of Simmons-Smith reactions using Zn carbenoids possessing beta-hydrogen atoms.

引用

页码：348 / 352

页数：5

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[31] The "Cyclopropyl Fragment" is a Versatile Player that Frequently Appears in Preclinical/Clinical Drug Molecules [J].