Chelated [3,3]-rearrangements of difluoroallylic alcohols

Autor:	Jonathan M. Percy, Michael E. Prime, Michael J. Broadhurst
Rok vydání:	1997
Předmět:	chemistry.chemical_classification Ketone Silylation Organic Chemistry chemistry.chemical_element Ketene Biochemistry Medicinal chemistry chemistry.chemical_compound chemistry Drug Discovery Propionate Organic chemistry Lithium Chelation
Zdroj:	Tetrahedron Letters. 38:5903-5906
ISSN:	0040-4039
DOI:	10.1016/s0040-4039(97)01315-4
Popis:	Whereas the lithium enolates of acetate and propionate esters of difluoroallylic alcohols fragment rapidly, even at −78 °C, methoxy- and benzyloxy-acetates form chelated enolates which undergo smooth [3,3]-rearrangement as their silyl ketene acetals. The latent ketone function can be revealed under mild conditions (MeOH, SOCl2) to afford very highly functionalised CF2 compounds.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::bfeba76d528eca6113c016bcde287dd9 https://doi.org/10.1016/s0040-4039(97)01315-4 Zobrazit plný text záznamu Full Text from ScienceDirect