Strain-Release [2π+2σ] Cycloadditions for the Synthesis of Bicyclo[2.1.1]hexanes Initiated by Energy Transfer

被引：207

作者：

Guo, Renyu ^{[1
]}

Chang, Yu-Che ^{[1
]}

Herter, Loic ^{[2
,3
]}

Salome, Christophe ^{[2
]}

Braley, Sarah E. ^{[1
]}

Fessard, Thomas C. ^{[2
]}

Brown, M. Kevin ^{[1
]}

机构：

[1] Indiana Univ, Dept Chem, Bloomington, IN 47405 USA

[2] SpiroChem AG, CH-4058 Basel, Switzerland

[3] Univ Strasbourg, LabEx Medalis, Biofunct Chem, UMR 7199, F-67400 Illkirch Graffenstaden, France

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2022年 / 144卷 / 18期

关键词：

CYCLOPROPYLAMINES; ANNULATION; DISCOVERY; ELECTRON;

D O I：

10.1021/jacs.2c02976

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Saturated bicycles are becoming ever more important in the design and development of new pharmaceuticals. Here a new strategy for the synthesis of bicyclo[2.1.1]hexanes is described. These bicycles are significant because they have defined exit vectors, yet many substitution patterns are underexplored as building blocks. The process involves sensitization of a bicyclo[1.1.0]butane followed by cycloaddition with an alkene. The scope and mechanistic details of the method are discussed.

引用

收藏

页码：7988 / 7994

页数：7

相关论文

共 72 条

[1] Enantioselective Photocatalytic [3+2] Cycloadditions of Aryl Cyclopropyl Ketones [J].

Amador, Adrian G. ;

Sherbrook, Evan M. ;

Yoon, Tehshik P. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (14) :4722-4725

[2] BICYCLO[1.1.0]BUTANES - REACTIONS WITH CYCLIC AZO-COMPOUNDS [J].

AMEY, RL ;

SMART, BE .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (20) :4090-4092

[3] POLAR SUBSTITUENT EFFECTS IN 1,3-DISUBSTITUTED BICYCLO[1.1.1]PENTANES [J].

APPLEQUIST, DE ;

RENKEN, TL ;

WHEELER, JW .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (25) :4985-4995

[4]

Beltran S., 2022, CHEMRXIV, V2022, DOI [10.26434/chemrxiv-2022-v93kv, DOI 10.26434/CHEMRXIV-2022-V93KV]

[5] Difunctionalization of C-C σ-Bonds Enabled by the Reaction of Bicyclo[1.1.0]butyl Boronate Complexes with Electrophiles: Reaction Development, Scope, and Stereochemical Origins [J].

Bennett, Steven H. ;

Fawcett, Alexander ;

Denton, Elliott H. ;

Biberger, Tobias ;

Fasano, Valerio ;

Winter, Nils ;

Aggarwal, Varinder K. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (39) :16766-16775

[6] BICYCLO[1.1.0]BUTANE CHEMISTRY .2. CYCLOADDITION REACTIONS OF 3-METHYLBICYCLO[1.1.0]BUTANECARBONITRILES . FORMATION OF BICYCLO[2.1.1]HEXANES [J].

CAIRNCROSS, A ;

BLANCHAR.EP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (03) :496-+

[7] Intramolecular donor-acceptor cyclopropane ring-opening cyclizations [J].

Cavitt, Marchello A. ;

Phun, Lien H. ;

France, Stefan .

CHEMICAL SOCIETY REVIEWS, 2014, 43 (03) :804-818

[8] 2,3-DIAZABICYCLO[2.1.1]HEX-2-ENE - SYNTHESIS AND THERMAL-DECOMPOSITION [J].

CHANG, MH ;

DOUGHERTY, DA .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (20) :4092-4093

[9] Synthetic Methods Driven by the Photoactivity of Electron Donor-Acceptor Complexes [J].

Crisenza, Giacomo E. M. ;

Mazzarella, Daniele ;

Melchiorre, Paolo .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (12) :5461-5476

[10] Enantioselective [2+2] Cycloadditions of Cinnamate Esters: Generalizing Lewis Acid Catalysis of Triplet Energy Transfer [J].

Daub, Mary Elisabeth ;

Jung, Hoimin ;

Lee, Byung Joo ;

Won, Joonghee ;

Baik, Mu-Hyun ;

Yoon, Tehshik P. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (24) :9543-9547

← 1 2 3 4 5 6 7 8 →