Mechanistic Investigations of Chiral Lithium Binaphtholate Catalysis for Asymmetric Aldol-Tishchenko Reaction of α-Fluoroarylketones

被引：0

作者：

Kotani, Shunsuke ^{[1
]}

Asano, Toshifumi ^{[1
]}

Arae, Sachie ^{[1
]}

Sugiura, Masaharu ^{[2
]}

Nakajima, Makoto ^{[1
]}

机构：

[1] Kumamoto Univ, Grad Sch Pharmaceut Sci, Kumamoto 8620973, Japan

[2] Sojo Univ, Fac Pharmaceut Sci, Kumamoto 8600082, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 23期

基金：

日本学术振兴会;

关键词：

ENANTIOSELECTIVE FLUORINATION; STEREOSELECTIVE-SYNTHESIS; DENSITY FUNCTIONALS; YB-COMPLEXES; KETONES; GENERATION; REDUCTION; CHEMISTRY; ALDEHYDES; CONSTRUCTION;

D O I：

10.1021/acs.joc.4c01404

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this study, we analyzed the asymmetric aldolTishchenko reaction of a-fluoroarylketones with aldehydes in the presence of chiral lithium binaphtholate, which was readily prepared from a chiral BINOL derivative and lithium tert-butoxide. This tandem reaction afforded enantiomerically enriched 2-fluoro-1,3-diols with three contiguous stereogenic centers in high yield and with high diastereo- and enantioselectivities. Moreover, mechanistic investigations of the lithium binaphtholate-catalyzed enantioselective aldol-Tishchenko reaction were performed based on the kinetic isotope effect and computational analyses.

引用

页码：17101 / 17114

页数：14

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