Concepedia

Catalytic Asymmetric Reverse Prenylation of Indol-2-one Enabled a Synthesis of (−)-Debromoflustramine A

Yi Hou, Jiyou Huo, Ruoxin Li, Jun Hou, Hongbo Wei, Weiqing Xie

Organic Letters · 2023 · 11 citations · 29 references

DOI

Concepts

Abstract

A catalytic asymmetric nucleophilic reverse prenylation of indol-2-ones in situ generated from 3-bromooxindoles with prenyltributylstannane promoted by Ni(II)/chiral N,N′ -dioxide was developed. This reaction provides facile access to C3 reverse-prenylated oxindoles in good to excellent enantioselectivities, which enabled the asymmetric synthesis of debromoflustramine A in five steps.

References

29

Chiral <i>N</i>,<i>N</i>′-Dioxides: New Ligands and Organocatalysts for Catalytic Asymmetric Reactions

Xiaohua Liu, Lili Lin, Xiaoming Feng · Accounts of Chemical Research · 2011 · 691 citations

, , +16

Asymmetric Cycloaddition and Cyclization Reactions Catalyzed by Chiral <i>N</i>,<i>N</i>′-Dioxide–Metal Complexes

Xiaohua Liu, Haifeng Zheng, Yong Xia et al. · Accounts of Chemical Research · 2017 · 470 citations

, , +15

Chiral N,N′-dioxide ligands: synthesis, coordination chemistry and asymmetric catalysis

Xiaohua Liu, Lili Lin, Xiaoming Feng · Organic Chemistry Frontiers · 2014 · 417 citations

, , +16

Catalytic Enantioselective Stereoablative Alkylation of 3‐Halooxindoles: Facile Access to Oxindoles with C3 All‐Carbon Quaternary Stereocenters

Sandy Ma, Xiaoqing Han, Shyam Krishnan et al. · Angewandte Chemie International Edition · 2009 · 210 citations

, , +10

Exercising Regiocontrol in Palladium-Catalyzed Asymmetric Prenylations and Geranylation: Unifying Strategy toward Flustramines A and B

Barry M. Trost, Sushant Malhotra, Walter H. Chan · Journal of the American Chemical Society · 2011 · 200 citations

, , +12