Umpolung of o-Hydroxyaryl Azomethine Ylides: Entry to Functionalized γ-Aminobutyric Acid under Phosphine Catalysis

被引：20

作者：

Chen, Qingqing ^{[1
]}

Bao, Yishu ^{[1
]}

Yang, Xiuqin ^{[1
]}

Dai, Zonghao ^{[1
]}

Yang, Fulai ^{[1
]}

Zhou, Qingfa ^{[1
]}

机构：

[1] China Pharmaceut Univ, State Key Lab Nat Med, Dept Organ Chem, Nanjing 210009, Jiangsu, Peoples R China

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 17期

基金：

中国国家自然科学基金;

关键词：

ELECTRON-DEFICIENT ALKYNES; ALPHA-AMINO-ACIDS; ASYMMETRIC 1,3-DIPOLAR CYCLOADDITION; ANTIFUNGAL CYCLIC-PEPTIDES; PHASE-TRANSFER CATALYSIS; DOMINO REACTIONS; STEREOSELECTIVE-SYNTHESIS; DECARBOXYLATIVE GENERATION; ENANTIOSELECTIVE SYNTHESIS; ALLYLIC ALKYLATIONS;

D O I：

10.1021/acs.orglett.8b02297

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A phosphine-catalyzed reaction between ohydroxyaryl azomethine ylides and MBH carbonates provides access to highly functionalized gamma-aminobutyric acid derivatives in moderate to good yields. Mechanistically, the reaction involves a phosphine-catalyzed tandem S(N)2'/2-aza-Cope rearrangement/intramolecular addition process.

引用

页码：5380 / 5383

页数：4

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