TBSOTf-promoted versatile N-formylation using DMF at room temperature
Hydrazides and amines were N-formylated by DMF in the presence of tert-butyldimethylsilyl triflate (TBSOTf) at room temperature, in good to excellent yields.
N-Acyl amino acid esters undergo triflic anhydride-mediated cyclodehydration to form oxazoles and bisoxazoles in a simple one-pot transformation.
Thalhammer, Armin,Mecinovi?, Jasmin,Schofield, Christopher J.
supporting information; experimental part
p. 1045 - 1047
(2009/05/31)
Enantioselective Rh-catalyzed hydrogenation of N-formyl dehydroamino esters with monodentate phosphoramidite ligands
Enantioselectivities up to >99% ee were achieved in the rhodium-catalyzed asymmetric hydrogenation of N-formyl dehydroamino esters using monodentate phosphoramidites as chiral ligands. The substrates were synthesized by condensation of methyl isocyanoacetate with a range of aldehydes and with cyclohexanone. A highly convenient multigram scale one step synthesis of methyl 2-(formamido)acrylate was developed. This compound was used in the synthesis of methyl 2-(formamido)cinnamate via a solvent free Heck reaction. Moreover, full conversion and >99% ee were obtained in 1 h in the hydrogenation of methyl 2-(formamido)acrylate with 0.2 mol% catalyst and 2 bar hydrogen pressure. The versatility of the formyl protection was established by its removal under mild conditions.
Panella, Lavinia,Aleixandre, Alicia Marco,Kruidhof, Gerlof J.,Robertus, Jort,Feringa, Ben L.,De Vries, Johannes G.,Minnaard, Adriaan J.
p. 2026 - 2036
(2007/10/03)
A simple and convenient synthesis of N-formyl amino acid esters under mild conditions
A variety of amino acid ester hydrochlorides react with cyanomethyl formate at room temperature to give the N-formyl amino acid esters in good yields and without racemization.
Duczek,Deutsch,Vieth,Niclas
p. 37 - 38
(2007/10/03)
Formyloxy-acetonitrile - A reagent for convenient N- and O-formylations
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Deutsch,Duczek,Niclas
p. 488 - 490
(2007/10/03)
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