Modulating the stereochemical outcome of the Ireland–Claisen reaction of (E)- and (Z)-allylic glycolates

Autor:	Ken S. Feldman, Brandon R. Selfridge
Rok vydání:	2012
Předmět:	chemistry.chemical_classification State model Allylic rearrangement Silylation Alkene Stereochemistry Organic Chemistry Ketene Biochemistry Glycolates chemistry.chemical_compound chemistry Drug Discovery Lewis acids and bases
Zdroj:	Tetrahedron Letters. 53:825-828
ISSN:	0040-4039
Popis:	The diastereoselectivity of Ireland–Claisen rearrangements of allylic glycolates is dependent on the E:Z ratio of the silyl ketene acetals, the alkene geometry in the allyl unit, and the transition state topography. High yields and excellent diastereoselectivities (>95:5) have been achieved for selected substrates, including those with R2 = ethyl that results in a newly formed quaternary center. A discussion of the scope, selectivities, and transition state models will be presented.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::ab92d5ec434648429772e5fbaf3d23f6 https://doi.org/10.1016/j.tetlet.2011.12.011 Zobrazit plný text záznamu Full Text from ScienceDirect