Organocatalytic Remote Stereocontrolled Synthesis of Tetrasubstituted Allenes via Asymmetric 1,8-Addition of Propargylic Aza-p-Quinone Methides

Yue，Zhibin1; Xia，Yan1; Shen，Boming2; Liu，Chang2; Yu，Peiyuan2; Li，Pengfei2; Li，Wenjun1

2024

10.1002/adsc.202301286

Advanced Synthesis and Catalysis   影响因子和分区

1615-4150

1615-4169

An organocatalytic remote stereocontrolled 1,8-conjugated addition of in situ formed propargylic aza-p-QMs from α-(4-aminophenyl) propargylic alcohols and indole-2-carboxylates was developed, affording axially chiral tetrasubstituted allenes in 62–99% yield with 52–99% ee. The synthetic strategy not only enriches the chemistry of aza-p-quinone methides, but also provides an alternative tool for the preparation of axially chiral tetrasubstituted allenes.

1,8-conjugated addition allenes aza-para-quinone methides organocatalysis

SCI

英语

其他

2-s2.0-85184191145

Scopus

1.Department of Medicinal Chemistry,School of Pharmacy,Qingdao University,Qingdao,Shandong,266021,China
2.Department of Chemistry,Guangdong Provincial Key Laboratory of Catalysis,College of Science,Southern University of Science and Technology Guangming Advanced Research Institute,Southern University of Science and Technology (SUSTech),Shenzhen,518055,China

Yue，Zhibin,Xia，Yan,Shen，Boming,et al. Organocatalytic Remote Stereocontrolled Synthesis of Tetrasubstituted Allenes via Asymmetric 1,8-Addition of Propargylic Aza-p-Quinone Methides[J]. Advanced Synthesis and Catalysis,2024,366(5):1078-1083.

Yue，Zhibin.,Xia，Yan.,Shen，Boming.,Liu，Chang.,Yu，Peiyuan.,...&Li，Wenjun.(2024).Organocatalytic Remote Stereocontrolled Synthesis of Tetrasubstituted Allenes via Asymmetric 1,8-Addition of Propargylic Aza-p-Quinone Methides.Advanced Synthesis and Catalysis,366(5),1078-1083.

Yue，Zhibin,et al."Organocatalytic Remote Stereocontrolled Synthesis of Tetrasubstituted Allenes via Asymmetric 1,8-Addition of Propargylic Aza-p-Quinone Methides".Advanced Synthesis and Catalysis 366.5(2024):1078-1083.