Gold-catalyzed efficient formation of alkenyl enol esters/carbonates from trimethylsilylmethyl-substituted propargyl esters/carbonates.
نویسندگان
چکیده
A gold-catalyzed efficient method for the preparation of alkenyl enol esters/carbonates is developed. Besides the mild reaction conditions and high catalytic efficiency, the excellent E-selectivity of the nonenolic double bond is remarkable.
منابع مشابه
Gold-catalyzed reactions of propargylic esters with vinylazides for the synthesis of Z- or E-configured buta-1,3-dien-2-yl esters.
Gold-catalyzed synthesis of buta-1,3-dien-2-yl esters by the reaction of propargyl esters with vinylazides is described; the reaction mechanism is postulated to involve a vinyl attack of vinylazides at alkenyl gold carbenes.
متن کاملChiral (acyclic diaminocarbene)gold(I)-catalyzed dynamic kinetic asymmetric transformation of propargyl esters.
A highly enantioselective transformation catalyzed by chiral (acyclic diaminocarbene)gold(I) complexes is reported. The enantioselective synthesis of 2-substituted chromenyl pivalates from racemic phenol-substituted propargyl pivalates was developed. Rearrangement of the substrates in the presence of cationic gold gave allene intermediates, whose cyclization resulted in formation of enantioenri...
متن کاملGold-catalyzed [3+3]-annulation of azomethine imines with propargyl esters.
The gold-catalyzed [3+3]-cycloaddition reaction of propargyl esters and azomethine imines has been developed. The reaction provides a rapid entry into a wide range of substituted tetrahydropyridazine derivatives from simple starting materials. A stepwise mechanism involving addition of the 1,3-dipole to a gold-carbenoid intermediate is proposed.
متن کاملHighly Efficient Gold(I)-Catalyzed Regio- and Stereoselective Hydrocarboxylation of Internal Alkynes
We report the highly efficient gold-catalyzed hydrocarboxylation of internal alkynes that operates under solvent- and silver-free conditions. This new, simple, and eco-friendly protocol allows for the synthesis of a wide variety of functionalized aryl and alkyl enol esters in high yields, with Z-stereospecificity and good regioselectivities and without the requirement for purification by chroma...
متن کاملHigh-Throughput Screening of the Asymmetric Decarboxylative Alkylation Reaction of Enolate-Stabilized Enol Carbonates.
The use of high-throughput screening allowed for the optimization of reaction conditions for the palladium-catalyzed asymmetric decarboxylative alkylation reaction of enolate-stabilized enol carbonates. Changing to a non-polar reaction solvent and to an electron-deficient PHOX derivative as ligand from our standard reaction conditions improved the enantioselectivity for the alkylation of a keta...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
عنوان ژورنال:
- Organic letters
دوره 8 20 شماره
صفحات -
تاریخ انتشار 2006