On the Configurational Stability and Reactivity of Tertiary Silyloxy Carbanions Derived from Stereoselective Brook Rearrangement

Autor:	Juan F. Collados, Syuzanna R. Harutyunyan, Pablo Ortiz
Rok vydání:	2016
Předmět:	010405 organic chemistry Concerted reaction Stereochemistry Chemistry Organic Chemistry Enantioselective synthesis Alkylation Brook rearrangement 010402 general chemistry 01 natural sciences 0104 chemical sciences Stereospecificity Electrophile Physical and Theoretical Chemistry Chirality (chemistry) Carbanion
Zdroj:	European Journal of Organic Chemistry. 2016:3065-3069
ISSN:	1434-193X
DOI:	10.1002/ejoc.201600493
Popis:	Here we report a stereospecific Brook rearrangement/trapping sequence, initiated by the formation of a zinc alkoxide from an enantioenriched (hydroxyallyl)silane. The chiral carbanion resulting from the Brook rearrangement is trapped intermolecularly by carbonyl electrophiles with complete transfer of chirality. A concerted mechanism is proposed to rationalize the stereospecificity observed in the reaction sequence.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::f8a832efb255af97965d67ebb024f38f https://doi.org/10.1002/ejoc.201600493 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
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