Control of Enantioselectivity in Rhodium(I) Catalysis by Planar Chiral Dibenzo[a,e]cyclooctatetraenes

Publisher： John Wiley & Sons Inc

E-ISSN： 1521-3765|24|10|2344-2348

ISSN： 0947-6539

Source： CHEMISTRY - A EUROPEAN JOURNAL, Vol.24, Iss.10, 2018-02, pp. : 2344-2348

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Abstract

AbstractPlanar 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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