Diastereoselective Hydroacylation of Cyclopropenes by Visible-Light Photocatalysis

被引：12

作者：

Biswas, Sourabh ^{[1
]}

Chandu, Palasetty ^{[1
]}

Garai, Sumit ^{[1
]}

Sureshkumar, Devarajulu ^{[1
]}

机构：

[1] Indian Inst Sci Educ & Res Kolkata, Dept Chem Sci, Mohanpur 741246, West Bengal, India

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 43期

关键词：

ALPHA-KETO ACIDS; CATALYZED CARBOZINCATION; MERGING PHOTOREDOX; ACYL RADICALS; CYCLOPROPANATION; ACYLATION; OXOCARBOXYLATES; DERIVATIVES; STRAIN;

D O I：

10.1021/acs.orglett.3c03095

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and general strategy for the hydroacylation of cyclopropene is disclosed for synthesizing various 2-acylcyclopropane derivatives under mild reaction conditions. High functional group tolerance of this protocol features a novel route to access a divergent synthesis of acylated cyclopropane in a diastereoselective manner by photoinduced decarboxylation of alpha-ketoacid followed by acyl radical addition to cyclopropene. Additionally, the regioselective addition of acyl radical at the least substituted olefinic carbon center with trans-selective fashion makes this protocol more appealing toward natural product development.

引用

页码：7863 / 7867

页数：5

共 48 条

[1] Peptide-Catalyzed Diastereo- and Enantioselective Cyclopropanation of Aromatic α,β-Unsaturated Aldehydes [J].

Akagawa, Kengo ;

Takigawa, Shota ;

Nagamine, Iman Sho ;

Umezawa, Ryota ;

Kudo, Kazuaki .

ORGANIC LETTERS, 2013, 15 (19) :4964-4967

[2] Put a ring on it: application of small aliphatic rings in medicinal chemistry [J].

Bauer, Matthias R. ;

Di Fruscia, Paolo ;

Lucas, Simon C. C. ;

Michaelides, Iacovos N. ;

Nelson, Jennifer E. ;

Storer, R. Ian ;

Whitehurst, Benjamin C. .

RSC MEDICINAL CHEMISTRY, 2021, 12 (04) :448-471

[3] Acyl Radicals from Aromatic Carboxylic Acids by Means of Visible-Light Photoredox Catalysis [J].

Bergonzini, Giulia ;

Cassani, Carlo ;

Wallentin, Carl-Johan .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (47) :14066-14069

[4] N-Heterocyclic Carbene (NHC)-Catalyzed Intermolecular Hydroacylation of Cyclopropenes [J].

Bugaut, Xavier ;

Liu, Fan ;

Glorius, Frank .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (21) :8130-8133

[5] Room-Temperature Decarboxylative Couplings of α-Oxocarboxylates with Aryl Halides by Merging Photoredox with Palladium Catalysis [J].

Cheng, Wan-Min ;

Shang, Rui ;

Yu, Hai-Zhu ;

Fu, Yao .

CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (38) :13191-13195

[6] Merging Photoredox and Nickel Catalysis: The Direct Synthesis of Ketones by the Decarboxylative Arylation of -Oxo Acids [J].

Chu, Lingling ;

Lipshultz, Jeffrey M. ;

MacMillan, David W. C. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (27) :7929-7933

[7] Regio- and Diastereoselective Carbometalation Reaction of Cyclopropenes [J].

Cohen, Yair ;

Marek, Ilan .

ACCOUNTS OF CHEMICAL RESEARCH, 2022, :2848-2868

[8] Stereoselective Synthesis of Polysubstituted Spiropentanes [J].

Cohen, Yair ;

Toledano, Dor ;

Marek, Ilan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (37) :16732-16736

[9] Pd-Catalyzed Enantioselective Hydroalkynylation of Cyclopropenes [J].

Dian, Longyang ;

Marek, Ilan .

ACS CATALYSIS, 2020, 10 (02) :1289-1293

[10] Visible-light photoredox catalyzed hydroacylation of electron-deficient alkenes: carboxylic anhydride as an acyl radical source [J].

Dong, Shupeng ;

Wu, Guibing ;

Yuan, Xiaoqian ;

Zou, Chuncheng ;

Ye, Jinxing .

ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (11) :2230-2234

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