59614-01-6Relevant articles and documents
Epoxide as precatalyst for metal-free catalytic transesterification
Tanaka, Shinji,Nakashima, Takuya,Satou,Oono, Hiromi,Kon, Yoshihiro,Tamura, Masanori,Sato, Kazuhiko
, p. 2009 - 2013 (2019/07/03)
Transesterification of methyl esters was accelerated by an in situ-generated metal-free catalyst comprising a quaternary alkylammonium salt and an epoxide. The combination of a quaternary alkylammonium acetate and glycidol is optimal, and various esters were synthesized from methyl esters with alcohols in good to excellent yield. Analysis of the catalyst solution revealed that basic species are generated by the ring-opening reaction of epoxide.
Highly enantioselective hydrogenation of 1-alkylvinyl benzoates: A simple, nonenzymatic access to chiral 2-alkanols
Kleman, Patryk,González-Liste, Pedro J.,García-Garrido, Sergio E.,Cadierno, Victorio,Pizzano, Antonio
, p. 16209 - 16212 (2013/12/04)
Going chiral! Highly enantioselective catalytic hydrogenations of enol esters 1 by using a Rh catalyst bearing a P?￡?OP ligand are described (see scheme; NBD=norbornadiene). The catalytic system has a broad scope and allows the preparation of a wide range of chiral esters 2 bearing diverse alkyls or a benzyl group with high enantioselectivities. These esters can easily be converted in highly enantioenriched 2-alkanols. Copyright
The role of acyloxyphosphonium ions and the stereochemical influence of base in the phosphorane-mediated esterification of alcohols
McNulty, James,Capretta, Alfredo,Laritchev, Vladimir,Dyck, Jeff,Robertson, Al J.
, p. 4051 - 4054 (2007/10/03)
Intimate details of the Mitsunobu mechanism: The trapping of an acyloxytributylphosphonium ion with a chiral secondary alcohol leads to either retention or inversion of stereochemistry in the resulting ester depending on the exclusion or inclusion of a base (see scheme). Insight into the mechanism of phosphorane-mediated esterification processes is presented.
