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1.
J Am Chem Soc ; 143(29): 11218-11224, 2021 07 28.
Artículo en Inglés | MEDLINE | ID: mdl-34270904

RESUMEN

The stereoselective cyanoalkylation of electron-deficient olefins with potassium cyanide and alkyl halides was developed based on the utilization of modular chiral 1,2,3-triazolium salts featuring a hydrogen bond-donor ability as catalysts. The reaction involving multiple carbon-carbon bond formations proceeds via the enantioselective conjugate addition of a cyanide ion and the consecutive catalyst-controlled diastereoselective alkylation of intermediary chiral triazolium enolates. Control experiments revealed that the use of a properly tuned chiral triazolium ion as a catalyst and the presence of the cyano functionality in the intermediary enolate are of crucial importance for achieving high levels of acyclic absolute and relative stereocontrol.

2.
J Am Chem Soc ; 133(5): 1307-9, 2011 Feb 09.
Artículo en Inglés | MEDLINE | ID: mdl-21204518

RESUMEN

Chiral 1,2,3-triazoliums have been designed, and the rational structural modification based on their unique anion-binding abilities has led to the establishment of the highly enantioselective alkylation of 3-substituted oxindoles.

3.
Chem Commun (Camb) ; 53(98): 13113-13116, 2017 Dec 07.
Artículo en Inglés | MEDLINE | ID: mdl-29094112

RESUMEN

A catalytic asymmetric alkylation of fully substituted enolates with racemic, non-activated secondary alkyl halides is described. The chiral 1,2,3-triazolium ion enables excellent diastereo- and enantiocontrol via enantiofacial discrimination of prochiral enolates and kinetic resolution of secondary halides.

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