Enantioselective Synthesis, Crystal Structures, and Stereoisomerism of Substituted o,m,o,p-Tetraphenylenes.

ABSTRACT: We have achieved the enantioselective synthesis of highly strained, substituted o,m,o,p-tetraphenylenes (≤98% ee) via the cationic Rh(I)/(R)-H₈-BINAP complex-catalyzed chemo-, regio-, and enantioselective intermolecular cross-[2+2+2] cycloaddition of teraryl diynes with dimethyl acetylenedicarboxylate. X-ray crystallographic analyses demonstrate the highly bent structures of the para-substituted benzene moieties, and density functional theory calculations reveal the large local strain of the paraphenylene unit. ¹H nuclear magnetic resonance analyses and theoretical calculations elucidate the stereoisomerism, indicating that the nonrotatable ortho-disubstituted biphenyl structure results in cis and trans is

SUBMITTER: Kawai Y 

PROVIDER: S-EPMC11421083 | biostudies-literature | 2024 Sep

REPOSITORIES: biostudies-literature