Citation: Haoran Hong, Hongyu Wang, Changwu Zheng, Gang Zhao, Yongjia Shang. Organophosphine bearing multiple hydrogen-bond donors for asymmetric Michael addition reaction of 1-oxoindane-2-carboxylic acid ester via dual-reagent catalysis[J]. Chinese Chemical Letters, ;2021, 32(2): 708-712. doi: 10.1016/j.cclet.2020.07.026 shu

Organophosphine bearing multiple hydrogen-bond donors for asymmetric Michael addition reaction of 1-oxoindane-2-carboxylic acid ester via dual-reagent catalysis

Haoran Hong ^a ,
Hongyu Wang ^c ,
Changwu Zheng ^b ,
Gang Zhao ^{b, *,} ,
Yongjia Shang ^{a, *,}

a.
Key Laboratory of Functionalized Molecular Solids, Ministry of Education, Anhui Key Laboratory of Molecule-Based Materials (State Key Laboratory Cultivation Base), College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, China
b.
Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Center for Excellence in Molecular Synthesis, Chinese Academy of Sciences, Shanghai 200032, China
c.
College of Chemistry, Chemical Engineering and Materials Science, Shandong Normal University, Ji'nan 250014, China

zhaog@sioc.ac.cn

shyj@mail.ahnu.edu.cn

Received Date: 20 May 2020
Revised Date: 1 July 2020
Accepted Date: 13 July 2020
Available Online: 15 July 2020

Figures(7)

Multiple hydrogen bonds containing nucleophilic phosphines derived from dipeptide dual-reagents catalyzed asymmetric Michael addition reactions between indene esters and activated olefins in high yields and good to excellent enantioselectivities under mild reaction conditions. The success of current highly selective reactions should provide inspiration for expansion to other reactions and would open up new paradigms for the synthesis of indanone derivatives bearing chiral quaternary carbon centers.
- Dual-reagent catalysis,
- Michael addition reaction,
- Multiple hydrogen bonds,
- Chiral quaternary carbon centers
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