Organocatalytic Asymmetric Atroposelective Construction of Axially Chiral 1,4-Distyrene 2,3-Naphthalene Diols

被引：52

作者：

Li, Shan ^{[1
]}

Xu, Da ^{[1
]}

Hu, Fangli ^{[1
]}

Li, Dongmei ^{[1
]}

Qn, Wenling ^{[1
]}

Yan, Hailong ^{[1
]}

机构：

[1] Chongqing Univ, Sch Pharmaceut Sci, Chongqing Key Lab Nat Prod Synth & Drug Res, Chongqing 401331, Peoples R China

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 23期

关键词：

ENANTIOSELECTIVE SYNTHESIS; MOLECULAR RECOGNITION; SUBSTRATE SCOPE; BINOL; ARYLATION; CATALYSIS; ALDEHYDES; DIETHYLZINC; EPOXIDATION; ALKYLATION;

D O I：

10.1021/acs.orglett.8b03398

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient organocatalytic construction of enantioenriched axially chiral 1,4-distyrene 2,3-naphthalene diols through the nucleophilic addition of a-amido sulfone to in situ generated vinylidene o-quinone methide is described. The reaction pathway was investigated by isolating reaction intermediates and performing a kinetic resolution process. Axially chiral 1,4-distyrene 2,3-naphthalene diol was used as the chiral ligand for the enantioselective addition of diethylzinc to naphthalene formaldehyde. The preliminary results revealed that these adducts could be potentially used as ligands in asymmetric synthesis.

引用

页码：7665 / 7669

页数：5

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