Enantioselective Synthesis of Axially Chiral 1,8-Diarylnaphthalenes by Rh-Catalyzed [2 + 2 + 2] Cycloaddition and
Takanori Shibata1, Hinako Nikawa1, Ema Kadosaka1
1Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku, Tokyo 169-8555, Japan.
Abstract:
Intermolecular [2 + 2 + 2] cycloaddition of 1-alkynyl-8-arylnaphthalenes with 1,6-diynes proceeded in the presence of Rh-chiral BINAP derivative catalysts to give axially chiral 1,8-diarylnaphthalenes in excellent yields along with up to perfect enantioselectivity. As the aryl moiety, we could introduce 1-pyrenyl and (dibenzo)carbazolyl groups in addition to substituted phenyl ones. 1-Aryl-8-(1-pyrenyl)naphthalenes exhibited high fluorescence quantum yields (up to Φ = 0.89) and circularly polarized luminescence (CPL) properties (|glum| = up to 1.6 × 10-3).
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