Solvent Directed Diastereodivergent Synthesis of Spiro-Oxindoles with Quaternary Carbon Center Forming

被引：2

作者：

Zhang, Yang ^{[1
]}

Liao, Qian ^{[1
]}

Liu, Jin-Yu ^{[1
]}

Yang, Ming-Wen ^{[1
]}

机构：

[1] Chengdu Univ Technol, Coll Mat & Chem & Chem Engn, Chengdu 610059, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 26卷 / 38期

关键词：

catalysis; diastereodivergent synthesis; quaternary carbon center; solvent effects; spiro-oxindole; ORGANOCATALYTIC ASYMMETRIC-SYNTHESIS; CRAFTS CASCADE REACTION; ALPHA; BETA-UNSATURATED ALDEHYDES; CYCLOADDITION REACTION; INDOLE ALKALOIDS; CONSTRUCTION; DERIVATIVES; CATALYSIS;

D O I：

10.1002/ejoc.202300787

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient method has been developed for the solvent-directed diastereodivergent cyclization reactions with quaternary center formation. Various spiro-oxindole diastereoisomers were synthesized with good yields (up to >99 %) and moderate to high diastereoselectivities (up to >20 : 1). Further study on NMR studies indicates that the key to this approach lies in different interactions between the substrate and organocatalyst across diverse solvents. This methodology may have significant implications for switchable, solvent-directed diastereodivergent synthesis.

引用

页数：7

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