1,3-Diethynylallenes (DEAs): Enantioselective Synthesis, Absolute Configuration, and Chiral Induction in 1,1,4,4-Tetracyanobuta-1,3-dienes (TCBDs)

被引：50

作者：

Alonso-Gomez, Jose Lorenzo ^{[1
]}

Schanen, Patrick ^{[1
]}

Rivera-Fuentes, Pablo ^{[1
]}

Seiler, Paul ^{[1
]}

Diederich, Francois ^{[1
]}

机构：

[1] ETH Zurich Honggerberg, Organ Chem Lab, HCI, CH-8093 Zurich, Switzerland

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2008年 / 14卷 / 34期

关键词：

allenes; chirality; circular dichroism; configuration determination; enantioselectivity;

D O I：

10.1002/chem.200801456

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A study was conducted to demonstrate enantioselective synthesis, absolute configuration, and chiral induction in 1,1,4,4-tetracyanobuta-1,3-dienes. The study demonstrated that 4-N,N-dimethylanilino (DMA) donor-substituted optically active DEAs undergo photoisomerization, leading to racemization. It was found that these 1,1,4,4-tetracyanobuta-1,3-dienes react in a facile [2+2] cycloaddition with tetracyanoethene (TCNE), to form optically active and photostable 1,1,4,4-tetracyanobuta-1,3-diene (TCBD) derivatives. Chiral induction from the optically active allene moiety in the TCBD chromophore was observed in these compounds by circular dichromism (CD) spectroscopy. More investigations were also conducted to improve the yield and the enantioselectivity of the synthesis of optically active DEAs.

引用

页码：10564 / 10568

页数：5

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