385765-91-3Relevant academic research and scientific papers
Reaction of α-(N-carbamoyl)alkylcuprates with enantioenriched propargyl electrophiles: Synthesis of enantioenriched 3-pyrrolines
Dieter, R. Karl,Chen, Ningyi,Gore, Vinayak K.
, p. 8755 - 8760 (2007/10/03)
Enantioenriched propargyl mesylates or perfluorobenzoates react with α-(N-carbamoyl)alkylcuprates to afford scalemic α-(N-carbamoyl) allenes which undergo N-Boc deprotection and AgNO3-promoted cyclization to afford N-alkyl-3-pyrrolines. The syn
Reaction of α-(N-carbamoyl)alkylcuprates with propargyl substrates: Synthetic route to α-amino allenes and Δ3-pyrrolines
Dieter, R. Karl,Chen, Ningyi,Yu, Huayun,Nice, Lois E.,Gore, Vinayak K.
, p. 2109 - 2119 (2007/10/03)
(Chemical Equation Presented) Carbamate deprotonation followed by treatment with CuCN·2LiCl affords α-(N-carbamoyl)-alkylcuprates which react with propargyl halides, mesylates, tosylates, phosphates, acetates, and epoxides to give α-(N-carbamoyl) allenes via an anti-SN2′ substitution process. Propargyl halides, sulfonates, and phosphates give good yields of carbamoyl allenes, while the acetates afford low yields. Propargyl substrates undergo regiospecific SN2′ substitution in the absence of severe steric hindrance. The α-(N-carbamoyl) allenes can be cyclized to 2-oxazolidinones or deprotected to afford the free amines which can be cyclized to Δ3-pyrrolines with either AgNO3 or Ru3(CO)12.
Synthesis of 3-pyrrolines, annulated 3-pyrrolines, and pyrroles from alpha-amino allenes.
Dieter,Yu
, p. 3855 - 3858 (2007/10/03)
Alpha-amino allenes, readily prepared from reaction of alpha-(N-carbamoyl)alkylcuprates with propargyl substrates followed by N-Boc deprotection, are converted in high yields to pyrrolines with AgNO(3). Palladium-catalyzed cyclization of amino allenes aff
