136291-66-2Relevant articles and documents
From bifunctional to trifunctional (tricomponent nucleophile-transition metal-lewis acid) catalysis: The catalytic, enantioselective α-fluorination of acid chlorides
Erb, Jeremy,Paull, Daniel H.,Dudding, Travis,Belding, Lee,Lectka, Thomas
scheme or table, p. 7536 - 7546 (2011/06/27)
We report in full detail our studies on the catalytic, asymmetric β-fluorination of acid chlorides, a practical method that produces an array of β-fluorocarboxylic acid derivatives in which improved yield and virtually complete enantioselectivity are controlled through electrophilic fluorination of a ketene enolate intermediate. We discovered, for the first time, that a third catalyst, a Lewis acidic lithium salt, could be introduced into a dually activated system to amplify yields of aliphatic products, primarily through activation of the fluorinating agent. Through our mechanistic studies (based on kinetic data, isotopic labeling, spectroscopic measurements, and theoretical calculations) we were able to utilize our understanding of this "trifunctional" reaction to optimize the conditions and obtain new products in good yield and excellent enantioselectivity.
Anomalous fluorinations of 3-aryl-2-hydroxypropanoic esters by diethylaminosulfur trifluoride (DAST)
Haigh, David,Jefcott, Lee J.,Magee, Katherine,McNab, Hamish
, p. 2895 - 2900 (2007/10/03)
Treatment of 3-aryl-2-hydroxypropanoic esters 8 with diethylaminosulfur trifluoride (DAST) gives considerable amounts of rearranged 2-aryl-3-fluoropropanoic esters 12 together with the expected products 11. The extent of rearrangement is dependent on solv
HYDROGENATION CATALYTIQUE D'ALDEHYDES; CETONES ET ESTERS α,β-ETHYLENIQUES α-FLUORES ET DE CETONES α,β-ETHYLENIQUES α,β-DIFLUORES
Martinet, Pascal,Sauvetre, Raymond,Normant, Jean-F.
, p. 419 - 432 (2007/10/02)
Reduction of α-fluoro α,β-unsaturated aldehydes, esters and ketones to the corresponding saturated compounds is readily achieved by catalytic hydrogenation on Pd/C.The same reduction with α,β-difluoro α,β-unsaturated ketones gives various results depending on the solvent.
