Aminative Umpolung cyclization for synthesis of chiral exocyclic vicinal diamines

文献情報

出版日 2018-09-26

DOI 10.1039/C8OB02000K

インパクトファクター 3.876

著者

Feng Liu, Guoqing Zhao, Weiqi Cai, Dongfang Xu, Baoguo Zhao

原文を見る

要旨

Chiral exocylic vicinal diamines are biologically and chemically important compounds, but they are not easy to make. In this paper, an interesting aminative Umpolung cyclization process has been developed. Aromatic aldehydes 6 bearing an electrophilic chiral sulfinimine group underwent imine formation with 2,2-diphenylglycine (2), decarboxylation, and subsequent Umpolung cyclization, producing various trans-diamines 10 in 84–96% yields with high trans/cis ratios under very mild conditions. This work not only provides an efficient, clean, and mild method for the synthesis of chiral exocyclic vicinal diamines in one step but also represents a new application of aminative Umpolung strategy on intramolecular reactions.

掲載誌

Organic & Biomolecular Chemistry

CiteScore: 3.4

自己引用率: 10.3%

年間論文数: 1041

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

Aminative Umpolung cyclization for synthesis of chiral exocyclic vicinal diamines

文献情報

おすすめジャーナル

関連文献

Fabrication of a self-assembled and flexible SERS nanosensor for explosive detection at parts-per-quadrillion levels from fingerprints

Quantitative analysis of multiple high-resolution mass spectrometry images using chemometric methods: quantitation of chlordecone in mouse liver

Contents list

Engineering molecularly imprinted polymers (MIPs) for the selective extraction and quantification of the novel psychoactive substance (NPS) methoxphenidine and its regioisomers

Back cover

Exploiting the conformational-selection mechanism to control the response kinetics of a “smart” DNA hydrogel

Analysis of poly(ADP-ribose) polymerase-1 by enzyme-initiated auto-PARylation-controlled aggregation of hemin-graphene nanocomposites

Quantitative colorimetric paper analytical devices based on radial distance measurements for aqueous metal determination

Raman imaging of heme metabolism in situ in macrophages and Kupffer cells

Front cover

こちらもおすすめ

3-イチチルビフェニルはどのように合成されますか？

8-溴-5-三氟甲基喹啉はどのように合成されますか？

ジメチル4-(4,4,5,5-テトラメチル-1,3,2-ドioxaborolan-2-基)-2,6-ピリジンジカルボイル酸フェニルアミニドの代替品はありますか？

N-(3,5-ヘキサクロロ-4-ピリドインイル)-8-メチオキシ-5-キノリンカーボン酸の市場動向や研究トレンドはどのようなものでしょうか？

イソステアロイルグリセリルは安全ですか？

1-(二苯甲基)-3,3-二氟-氮杂环丁烷の市場動向や研究トレンドはどうですか？

3-チオフェンスチオールの物理化学的性質は何ですか？

2-Methyl-2-propanyl (2S)-2-(aminomethyl)-1-piperidinecarboxylateは安全ですか？

CAS番号1316822-90-8の化合物は安全ですか？

Tert-butyl 2-(2-羟基乙基)哌嗪-1-羧酸はどのように保存すればよいですか？

掲載誌

Organic & Biomolecular Chemistry

おすすめ化合物

tert-Butyl 4-cyanophenethylcarbamate

PS 1145 Dihydrochloride

5-(2-Thienyl)-1,2-oxazole-3-carbohydrazide

1-[6-(1H-Imidazol-1-yl)-3-pyridinyl]methanamine

1-oxaspiro[4.4]nonan-6-one

おすすめサプライヤー