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
收藏
页码：348 / 352
页数：5
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