Chemistry - A European Journal p. 2344 - 2348 (2018)
Update date:2022-09-26
Topics:
Melcher, Michaela-Christina
Iv?i?, Trpimir
Olagnon, Charlotte
Tenten, Christina
Lützen, Arne
Strand, Daniel
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.
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