Citation: Haijun Leng, Zhao Qian, Qing Mao, Shuaijiang Liu, Menglan Luo, Rui Qin, Wei Huang, Gu Zhan. NHC-catalysed retro-aldol/aldol cascade reaction enabling solvent-controlled stereodivergent synthesis of spirooxindoles[J]. Chinese Chemical Letters, ;2021, 32(8): 2567-2571. doi: 10.1016/j.cclet.2021.03.009 shu

NHC-catalysed retro-aldol/aldol cascade reaction enabling solvent-controlled stereodivergent synthesis of spirooxindoles

Haijun Leng ^{a, b, 1} ,
Zhao Qian ^{a, 1} ,
Qing Mao ^a ,
Shuaijiang Liu ^a ,
Menglan Luo ^a ,
Rui Qin ^a ,
Wei Huang ^{a, *,} ,
Gu Zhan ^{a, *,}

a.
State Key Laboratory of Southwestern Chinese Medicine Resources, School of Pharmacy and School of Basic Medical Sciences, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, China
b.
Antibiotics Research and Re-evaluation Key Laboratory of Sichuan Province, Sichuan Industrial Institute of Antibiotics, School of Pharmacy, Chengdu University, Chengdu 610052, China

huangwei@cdutcm.edu.cn

zhangu@cdutcm.edu.cn

Received Date: 25 December 2020
Revised Date: 2 March 2021
Accepted Date: 3 March 2021
Available Online: 5 March 2021

Figures(5)

An N-heterocyclic carbene (NHC)-catalysed retro-aldol/aldol cascade reaction of spirooxindole-based β-hydroxyaldehyde has been developed. The ring opening-closure process enables the diastereodivergent synthesis of spirocyclopentaneoxindole products with four consecutive stereocenters by simply changing the reaction solvents (THF or DCE). The Michael/aldol/retro-aldol/aldol sequential protocol allows the diastereodivergent synthesis of spirocyclopentaneoxindoles from 3-substituted oxindole and α, β-unsaturated aldehyde under the relay catalysis of a chiral secondary amine and an NHC catalyst. Moreover, four stereoisomers of the product can be selectively provided by using different combinations of a chiral secondary amine and a solvent.
- Asymmetric synthesis,
- Solvent-controlled diastereodivergence,
- Retro-aldol/aldol,
- Cascade reaction,
- Spirooxindole,
- N-Heterocyclic carbene catalysis
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