Cobalt Catalyzed Reductive Spirocyclopropanation Reactions. Issue 2 (22nd November 2019)

• Record Type: Journal Article
• Authors: Werth, Jacob; Berger, Kristen; Uyeda, Christopher
• Is Part Of: Advanced synthesis & catalysis. Volume 362:Issue 2(2020)
• Page Start: 348
• Page End: 352
• Publication Date: 2019-11-22
• Subjects: cyclopropanes -- spiro compounds -- cobalt -- carbenes -- carbenoids; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201901293
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: 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 β‐hydrogen atoms. Abstract :