Asymmetric Induction via a Helically Chiral Anion: Enantioselective Pentacarboxycyclopentadiene Bronsted Acid-Catalyzed Inverse-Electron-Demand Diels-Alder Cycloaddition of Oxocarbenium Ions

被引：49
作者：
Gheewala, Chirag D. [1 ]
Hirschi, Jennifer S. [2 ]
Lee, Wai-Hang [1 ]
Paley, Daniel W. [1 ]
Vetticatt, Mathew J. [2 ]
Lambert, Tristan H. [1 ,3 ]
机构：
[1] Columbia Univ, Dept Chem, New York, NY 10027 USA
[2] Binghamton Univ, Dept Chem, Binghamton, NY 13902 USA
[3] Cornell Univ, Dept Chem & Chem Biol, Ithaca, NY 14853 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2018年 / 140卷 / 10期
关键词：
ORTHO-QUINONE METHIDES; PHOSPHORIC-ACID; BOND DONORS; ALKYNYLATION; ETHERS; TRANSFORMATION; DERIVATIVES; ACTIVATION; ALDEHYDES; ADDITIONS;
D O I：
10.1021/jacs.8b00260
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An enantioselective catalytic inverse-electron-demand Diels-Alder reaction of salicylaldehyde acetal-derived oxocarbenium ions and vinyl ethers to generate 2,4-dioxychromanes is described. Chiral pentacarboxycyclopentadiene (PCCP) acids are found to be effective for a variety of substrates. Computational and X-ray crystallographic analyses support the unique hypothesis that an anion with point-chirality-induced helical chirality dictates the absolute sense of stereochemistry in this reaction.
引用
收藏
页码：3523 / 3527
页数：5
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