Stereoselective synthesis of alpha,alpha'-biprolines.
A means to induce dehydrodimerization of Seebach's oxazolidinone (5), the stereochemical outcome of which is entirely temperature dependent, is described. The resultant dimers 3 and 4 are precursors to (R,R)-alpha,alpha'-biproline (1) and meso-alpha,alpha'-biproline (2), respectively. An organohypobromite and an iminium halide are proposed to serve as electrophiles in the reaction with the enolate of 5 to give 3 and 4, respectively.
Vartak
Ashish P
AP
Department of Medicinal Chemistry, University of Minnesota, 308 Harvard Street SE, Minneapolis, Minnesota 55455, USA.
Young
Victor G
VG
Johnson
Rodney L
RL
D018360:Crystallography, X-Ray; D019281:Dimerization; D004151:Dipeptides / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D011392:Proline / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D004151:Dipeptides; D011392:Proline