Claisen Rearrangement of Aliphatic Allyl Vinyl Ethers from 1912 to 2012: 100 Years of Electrophilic Catalysis

被引：49

作者：

Rehbein, Julia ^{[1
]}

Hiersemann, Martin ^{[2
]}

机构：

[1] Univ Hamburg, Inst Organ Chem, Fachbereich Chem, D-20146 Hamburg, Germany

[2] Tech Univ Dortmund, Fak Chem, D-44227 Dortmund, Germany

来源：

SYNTHESIS-STUTTGART | 2013年 / 45卷 / 09期

关键词：

pericyclic reaction; rearrangement; catalysis; asymmetric catalysis; Lewis acids; TRANSITION-STATE STRUCTURE; NATURAL-PRODUCT SYNTHESIS; LEWIS-ACID; ASYMMETRIC-SYNTHESIS; ENOL ETHERS; STEREOSELECTIVE CONSTRUCTION; ENANTIOSELECTIVE SYNTHESIS; STEREOCHEMICAL CONTROL; CYCLIC 1,2-DIKETONES; AQUEOUS ACCELERATION;

D O I：

10.1055/s-0032-1316869

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This review summarizes, from a personal perspective, the development of catalytic asymmetric Claisen rearrangements from 1912 to 2012. 1 Introduction 2 Gosteli-Claisen Rearrangement 3 Claisen Rearrangement Using Stable Enols: Kojic Acid and Diosphenols 4 The Early Years: Catalysis by Bronsted Acids 5 Lewis Acid Mediated Claisen Rearrangements: The Aluminum Age 6 Catalysis by Precious Metals 7 Catalysis by sigma-Lewis Acids 8 Catalysis by Achiral Organocatalysts 9 Catalytic Asymmetric Claisen Rearrangements 10 Conclusion

引用

页码：1121 / 1159

页数：39

共 32 条

[31] ACID CATALYSIS OF CLAISEN REARRANGEMENT .1. FORMATION OF 4,4'-BIS (2H-CHROMENYL)MERCURY DERIVATIVES FROM ARYL 2-PROPYNYL ETHERS
BATES, DK
JONES, MC
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (19): : 3775 - 3776
[32] Gold(I)-Catalyzed Claisen Rearrangement of Allenyl Vinyl Ethers: Missing Transition States Revealed through Evolution of Aromaticity, Au(I) as an Oxophilic Lewis Acid, and Lower Energy Barriers from a High Energy Complex
Vidhani, Dinesh V.
Cran, John W.
Krafft, Marie E.
Manoharan, Mariappan
Alabugin, Igor V.
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (05): : 2059 - 2073

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