NHC-catalysed retro-aldol/aldol cascade reaction enabling solvent-controlled stereodivergent synthesis of spirooxindoles |
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Affiliation: | 1. 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;2. Antibiotics Research and Re-evaluation Key Laboratory of Sichuan Province, Sichuan Industrial Institute of Antibiotics, School of Pharmacy, Chengdu University, Chengdu 610052, China |
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Abstract: | 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. |
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Keywords: | Asymmetric synthesis Solvent-controlled diastereodivergence Cascade reaction Spirooxindole |
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