The Grob/Eschenmoser fragmentation of cycloalkanones bearing β-electron withdrawing groups: a general strategy to acyclic synthetic intermediates

Autor:	Tina Hsia, David W. Lupton, Judith Hierold
Rok vydání:	2011
Předmět:	Fragmentation (mass spectrometry) Nucleophile Chemistry Organic Chemistry Polar effect Organic chemistry Large range Physical and Theoretical Chemistry Ring (chemistry) Biochemistry Medicinal chemistry Eschenmoser fragmentation
Zdroj:	Org. Biomol. Chem.. 9:783-792
ISSN:	1477-0539 1477-0520
DOI:	10.1039/c0ob00632g
Popis:	Introduction of a β-electron withdrawing group to cycloalkanones allows facile C–C bond fragmentation. The reaction has been demonstrated with a large range of ring sizes, bearing various leaving and electron withdrawing groups, and using a variety of nitrogen and oxygen containing nucleophiles (>30 examples). The application of fragmentation products to the preparation of substituted γ-lactones has been demonstrated. Mechanistic studies are reported which are suggestive of a Grob/Eschenmoser type reaction.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::b052587ba79ab8d6b4ab75fd5d1e2f88 https://doi.org/10.1039/c0ob00632g Zobrazit plný text záznamu