From Allylic Sulfoxides to Allylic Sulfenates: Fifty Years of a Never-Ending [2,3]-Sigmatropic Rearrangement

被引：55

作者：

Colomer, Ignacio ^{[1
]}

Velado, Marina ^{[1
]}

Fernandez de la Pradilla, Roberto ^{[1
]}

Viso, Alma ^{[1
]}

机构：

[1] CSIC, Inst Quim Organ Gen, Consejo Super Invest Cient, Juan Cierva 3, E-28006 Madrid, Spain

来源：

CHEMICAL REVIEWS | 2017年 / 117卷 / 24期

关键词：

2,3 SIGMATROPIC REARRANGEMENT; DIELS-ALDER REACTIONS; ENANTIOMERICALLY PURE DIASTEREOMERS; ENANTIOSELECTIVE TOTAL-SYNTHESIS; STEREOSELECTIVE TOTAL SYNTHESES; METHYLENE-GAMMA-BUTYROLACTONES; MISLOW-EVANS REARRANGEMENT; ASYMMETRIC TOTAL-SYNTHESIS; FORMAL TOTAL-SYNTHESIS; STEREOCONTROLLED SYNTHESIS;

D O I：

10.1021/acs.chemrev.7b00428

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The [2,3]-sigmatropic rearrangement of allylic sulfoxides to allylic sulfenates is a reversible process, generally shifted toward the sulfoxide. In the presence of thiophiles, the sulfenate is trapped, and allylic alcohols are obtained under mild conditions. In most cases, a good transfer of stereochemical information through an ordered transition state is obtained. Furthermore, the ease of coupling this process with other versatile, stereocontrolled reactions has enhanced the usefulness of this protocol. This review aims to provide a comprehensive survey of this rearrangement and its application in the synthesis of natural and bioactive products.

引用

页码：14201 / 14243

页数：43

共 4 条

[1] Synthesis of alkyl allenyl sulfoxides from thiosuccinimides via [2,3]-sigmatropic rearrangement
Riddell, Adam B.
Michalski, Michelle M.
Schwan, Adrian L.
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2023, 198 (06) : 493 - 501
[2] Aryl Sulfoxides from Allyl Sulfoxides via [2,3]-Sigmatropic Rearrangement and Domino Pd-Catalyzed Generation/Arylation of Sulfenate Anions
Bernoud, Elise
Le Duc, Gaetan
Bantreil, Xavier
Prestat, Guillaume
Madec, David
Poli, Giovanni
ORGANIC LETTERS, 2010, 12 (02) : 320 - 323
[3] N-Sulfanylimides as the Sulfur Source for Alkyl Allenyl Sulfoxides via [2,3]-Sigmatropic Rearrangement
Riddell, Adam B.
Michalski, Michelle M.
Snowdon, Monika R.
Hirst, Mark J.
Schwan, Adrian L.
CHEMISTRYSELECT, 2021, 6 (41): : 11331 - 11336
[4] Synthesis of Enantiopure 3-Hydroxypiperidines from Sulfinyl Dienyl Amines by Diastereoselective Intramolecular Cyclization and [2,3]-Sigmatropic Rearrangement
Simal, Carmen
Bates, Robert H.
Urena, Mercedes
Gimenez, Irene
Koutsou, Christina
Infantes, Lourdes
Fernandez de la Pradilla, Roberto
Viso, Alma
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (15) : 7674 - 7692

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