Stereochemistry and Mechanism of the Ring-Opening Reaction of Cyclopropylenones with LiCu(Me)2

Autor:	Alan J. Shusterman, Mark C. Cesa, Charles P. Casey
Rok vydání:	2012
Předmět:	Chemistry Stereochemistry Chemical shift Organic Chemistry Ring (chemistry) Reductive elimination Cyclopropane Inorganic Chemistry chemistry.chemical_compound Proton NMR Ethyl group Physical and Theoretical Chemistry Enone Conjugate
Zdroj:	Organometallics. 31:7849-7854
ISSN:	1520-6041 0276-7333
Popis:	The chemical shifts of the diastereotopic hydrogens of the ethyl group of the cyclopropane ring-opening product of conjugate addition of LiCu(CH3)2 to cyclopropyl enone 1 were computed. Comparison of computed and observed 1H NMR chemical shifts of the diastereotopic hydrogens of the ethyl group of 2 established the stereochemistry of the ring-opening product as 2d-b. This provides evidence that the reaction proceeds by conjugate addition of the cuprate to the enone, followed by ring-opening of the cyclopropylmethyl copper species and reductive elimination.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::6e2788f450173c98148ee3ae967be416 https://doi.org/10.1021/om300520r Zobrazit plný text záznamu