Enantioselective Redox-Divergent Chiral Phosphoric Acid Catalyzed Quinone Diels-Alder Reactions

被引：29
|
作者：
Varlet, Thomas [1 ]
Gelis, Coralie [1 ]
Retailleau, Pascal [1 ]
Bernadat, Guillaume [2 ]
Neuville, Luc [1 ]
Masson, Geraldine [1 ]
机构：
[1] Univ Paris Saclay, CNRS, Inst Chim Subst Nat, 1 Ave Terrasse, F-91198 Gif Sur Yvette, France
[2] Fac Pharm Biocis 8076, LabEx LERMIT, Lab Chim Therapeut, 5 Rue JB Clement, F-92296 Chatenay Malabry, France
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2020年 / 59卷 / 22期
关键词：
cycloaddition; Diels-Alder reaction; hydrogen bonding; organocatalysis; synthetic methods; PERCHLORATE-DIETHYL-ETHER; BRONSTED ACID; REDUCTION POTENTIALS; ASYMMETRIC-SYNTHESIS; TITANIUM COMPLEX; NATURAL-PRODUCTS; LEWIS-ACID; IN-SITU; OXIDATION; REGIOSELECTIVITY;
D O I：
10.1002/anie.202000838
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An efficient enantioselective construction of tetrahydronaphthalene-1,4-diones as well as dihydronaphthalene-1,4-diols by a chiral phosphoric acid catalyzed quinone Diels-Alder reaction with dienecarbamates is reported. The nature of the protecting group on the diene is key to the success of achieving high enantioselectivity. The divergent "redox" selectivity is controlled by using an adequate amount of quinones. Reversible redox switching without erosion of enantioselectivity was possible from individual redox isomers.
引用
收藏
页码：8491 / 8496
页数：6
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