Stereoselective Synthesis of Cyclohexane Derivatives: Tandem Lithium Iodide Mediated Intramolecular Conjugate Addition of Thiols to α,β-Bisenones

被引：0

作者：

Jeon, Minseok ^{[1
]}

Yun, Chaeyoung ^{[2
]}

Seo, SungYong ^{[1
,2
]}

机构：

[1] Pukyong Natl Univ, Dept Chem, Busan 48513, South Korea

[2] Pukyong Natl Univ, Dept Smart Green Technol Engn, Busan 48513, South Korea

来源：

SYNTHESIS-STUTTGART | 2022年 / 54卷 / 12期

基金：

新加坡国家研究基金会;

关键词：

stereoselectivity; tandem conjugate addition; lithium iodide; alpha; beta-bisenones; thiols; RAUHUT-CURRIER REACTION; ACID; CYCLOPROPANATION; ELABORATION; ALLYLATION; REACTIVITY; ALCOHOLS; HALIDES; AMINES; WATER;

D O I：

10.1055/a-1754-7424

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A tandem intramolecular conjugate addition reaction was conducted with alpha,beta-bisenones as selected Michael acceptors which were converted into 1,2,3-trisubstituted six-membered rings in the presence of activated sulfur nucleophiles. The products were obtained in good to excellent yields (maximum yield: 99%). Various substituted alpha,beta-bisenones and sulfur nucleophiles were examined to understand the substrate scope of the reaction. Only one diastereomer was isolated, as lithium iodide mediated enolate trapping reactions improve the stereoselectivity of reactions involving 1,2,3-trisubstituted cyclohexanes.

引用

页码：2865 / 2875

页数：11

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