252681-06-4Relevant articles and documents
Rhodium-catalyzed Reformatsky-type reaction for asymmetric synthesis of difluoro-β-lactams using menthyl group as a chiral auxiliary
Tarui, Atsushi,Ozaki, Daiki,Nakajima, Naoko,Yokota, Yuto,Sokeirik, Yasser S.,Sato, Kazuyuki,Omote, Masaaki,Kumadaki, Itsumaro,Ando, Akira
, p. 3839 - 3843 (2008/09/21)
We developed a new methodology for the asymmetric Reformatsky-type reaction of (-)-menthyl bromodifluoroacetate (2) with imine in the presence of RhCl(PPh3)3. Ester 2 with the cost-effective chiral auxiliary gave (S)-difluoro-β-lacta
Enantioselective synthesis of α,α-difluoro-β-amino acid and 3,3- difluoroazetidin-2-one via the reformatsky-type reaction of ethyl bromodifluoroacetate with chiral 1,3-oxazolidines
Marcotte, Stephane,Pannecoucke, Xavier,Feasson, Christian,Quirion, Jean-Charles
, p. 8461 - 8464 (2007/10/03)
Chiral oxazolidines 2a-e can be diastereoselectively alkylated with BrCF2CO2Et to furnish 3,3-difluoroazetidin-2-ones 3a-e with up to 99% de. Selective cleavage of the chiral appendage provided the corresponding unsubstituted azetidinones. Formation of optically pure α,α-difluoro-β- amino acids 5a-c can be achieved by acidic hydrolysis of N-vinyl-azetidin-2- ones.