67761-47-1Relevant academic research and scientific papers
Control of Enantioselectivity in Rhodium(I) Catalysis by Planar Chiral Dibenzo[a,e]cyclooctatetraenes
Melcher, Michaela-Christina,Iv?i?, Trpimir,Olagnon, Charlotte,Tenten, Christina,Lützen, Arne,Strand, Daniel
supporting information, p. 2344 - 2348 (2017/12/26)
Planar chiral 5,11-disubstiuted dibenzo[a,e]cyclo-octatetraenes (dbCOTs) have been developed as the first useful chiral homologs to dbCOT-ligands for asymmetric applications. Methods enabling the preparation of such compounds on a gram-scale in enantiomerically pure form are described. Evaluated as ligands in rhodium(I)-catalyzed 1,4- and 1,2-arylation reactions, tertiary and quarternary stereogenic centers were formed with excellent yields and selectivities of up to >99 % ee. A catalytic asymmetric synthesis of a key cyclization precursor to (?)-penifulvin A highlights the system in an applied context.
