Enantioselective Copper‐Catalyzed Three‐Component Carboboronation of Allenes: Access to Functionalized Dibenzo [b,f][1,4]oxazepine Derivatives

A copper‐catalyzed enantioselective three‐component difunctionalization of allenes with seven‐membered cyclic imines and bis(pinacolato)diboron (B2(Pin)2) to approach functionalized dibenzo[b,f][1,4]oxazepine derivatives is developed. The chiral products are obtained in up to 81% yield, >20:1 dr,...

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Veröffentlicht in:Advanced synthesis & catalysis 2019-08, Vol.361 (15), p.3582-3587
Hauptverfasser: Deng, Hao, Meng, Ziwei, Wang, Sifan, Zhang, Zheming, Zhang, Yaqi, Shangguan, Yu, Yang, Fazhou, Yuan, Dekai, Guo, Hongchao, Zhang, Cheng
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Sprache:eng
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Zusammenfassung:A copper‐catalyzed enantioselective three‐component difunctionalization of allenes with seven‐membered cyclic imines and bis(pinacolato)diboron (B2(Pin)2) to approach functionalized dibenzo[b,f][1,4]oxazepine derivatives is developed. The chiral products are obtained in up to 81% yield, >20:1 dr, and 98% ee when either a chiral diphosphine ligand or a chiral ferrocenyl‐based P,N‐ligand is used. Furthermore, the reaction exhibits reversed diastereoselectivities when the chiral diphosphine ligand and the chiral P,N‐ligand are used respectively.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201900503