Citation: Li Miao, Chen Pingping, Chen Zhiming. Synthesis of Spirotetrahydrothiophene Compounds Catalyzed by Bifunctional Chiral Thiourea[J]. Chemistry, ;2019, 82(11): 1019-1026. shu

Synthesis of Spirotetrahydrothiophene Compounds Catalyzed by Bifunctional Chiral Thiourea

Key Laboratory of Functional Materials Chemistry of Guizhou Province, School of Chemistry and Materials Science, Guizhou Normal University, Guiyang 550001

Corresponding author: Chen Zhiming, czm000219@163.com
Received Date: 24 May 2019
Accepted Date: 3 August 2019

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In this paper, three kinds of multi-hydrogen bond-axis chiral naphthol thiourea were synthesized and used to catalyze the Sulfa-Michael/Aldol reaction of 1, 4-dithiane-2, 5-diol and α, β-unsaturated ketone. Asymmetric synthesis of spiro[tetrahydrothiophene-3-ol] compounds was achieved and the reaction conditions were optimized. When THF is used as solvent, the dosage of catalyst 1a is 20(mol)%, the temperature and reaction time are 25℃ and 8 h, the target products can be obtained with high yield (up to 92%) and good stereoselectivity (up to 85%) and diastereoselectivity (>90:10 dr).
- Axonal thiourea,
- Bifunctional,
- 1, 4-Dithiane-2, 5-diol,
- α, β-unsaturated ketone
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