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

作　　者：Haijun Leng Qian Zhao Qing Mao Shuaijiang Liu Menglan Luo Rui Qin Wei Huang Gu Zhan 

机构地区：[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

出　　处：《Chinese Chemical Letters》2021年第8期2567-2571,共5页中国化学快报（英文版）

基　　金：financial support from Ministry of Science and Technology of China (No.2019ZX09721001-008);National Natural Science Foundation of China (Nos.81773890,22001024,82073997);the “Thousand Talents Program” of Sichuan Province and Xinglin Scholar Research Premotion Project of CDUTCM。

摘　　要：An N-heterocyclic carbene(NHC)-catalysed retro-aldol/aldol cascade reaction of spirooxindole-basedβ-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 andα,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.

关 键 词：Asymmetric synthesis Solvent-controlled diastereodivergence Retro-aldol/aldol Cascade reaction SPIROOXINDOLE N-Heterocyclic carbene catalysis 

分 类 号：O626.13[理学—有机化学]