Catalytic Asymmetric Synthesis of Inherently Chiral Saddle-Shaped Dibenzo[b,f][1, 5]diazocines
Jinmiao Zhou , Mengyao Tang , Xiaoyu Yang
Chinese Journal of Chemistry ›› 2024, Vol. 42 ›› Issue (17) : 1953 -1959.
Catalytic Asymmetric Synthesis of Inherently Chiral Saddle-Shaped Dibenzo[b,f][1, 5]diazocines
Dibenzo[ b, f][1, 5]diazocines are a class of eight-membered heterocycles, which exhibit unique rigid saddle-shaped structure and possess inherent chirality. In this study, we report a convenient and straightforward method for the catalytic enantioselective synthesis of these unique chiral molecules through chiral phosphoric acid-catalyzed dimerization of 2-acylbenzoisocyanates. Notably, the addition of corresponding 2-acylaniline as the co-catalyst significantly improved the efficiency of these reactions, and a simple phase separation operation resulted in products with excellent enantiopurity. Experimental studies were performed to elucidate the mechanism behind these reactions, leading to the proposal of a plausible reaction mechanism based on the study findings.
Dibenzo[ b, f][1, 5]diazocines / Saddle-shaped inherent chirality / Organocatalysis / Asymmetric catalysis / Medium-ring compounds / Cooperative catalysis / Chiral phosphoric acids
2024 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
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