Stereoselective Synthesis of Cyclobutanes by Contraction of Pyrrolidines

被引：112

作者：

Hui, Chunngai ^{[1
,2
]}

Brieger, Lukas ^{[2
]}

Strohmann, Carsten ^{[2
]}

Antonchick, Andrey P. ^{[1
,2
,3
]}

机构：

[1] Max Planck Inst Mol Physiol, Dept Chem Biol, D-44227 Dortmund, Germany

[2] Tech Univ Dortmund, Fac Chem & Chem Biol, D-44221 Dortmund, Germany

[3] Nottingham Trent Univ, Sch Sci & Technol, Dept Chem & Forens, Nottingham NG11 8NS, England

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2021年 / 143卷 / 45期

关键词：

DIRECT SPECTROSCOPIC OBSERVATION; ENANTIOSELECTIVE TOTAL-SYNTHESIS; ELECTROPHILIC NH; N-(2,2,5,5-TETRAMETHYLPYRROLIDYL)NITRENE; PHOTOCHEMISTRY; REARRANGEMENT; 1,1-DIAZENES; SULFOXIMINES;

D O I：

10.1021/jacs.1c10175

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Here we report a contractive synthesis of multisubstituted cyclobutanes containing multiple stereocenters from readily accessible pyrrolidines using iodonitrene chemistry. Mediated by a nitrogen extrusion process, the stereospecific synthesis of cyclobutanes involves a radical pathway. Unprecedented unsymmetrical spirocyclobutanes were prepared successfully, and a concise, formal synthesis of the cytotoxic natural product piperarborenine B is reported.

引用

页码：18864 / 18870

页数：7

共 70 条

[1] Exploiting [2+2] cycloaddition chemistry: achievements with allenes [J].

Alcaide, Benito ;

Almendros, Pedro ;

Aragoncillo, Cristina .

CHEMICAL SOCIETY REVIEWS, 2010, 39 (02) :783-816

[2] Asymmetric Total Synthesis of (-)-Arborisidine and (-)-19-epi-Arborisidine Enabled by a Catalytic Enantioselective Pictet-Spengler Reaction [J].

Andres, Remi ;

Wang, Qian ;

Zhu, Jieping .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (33) :14276-14285

[3] Highly enantioselective synthesis and cellular evaluation of spirooxindoles inspired by natural products [J].

Antonchick, Andrey P. ;

Gerding-Reimers, Claas ;

Catarinella, Mario ;

Schuermann, Markus ;

Preut, Hans ;

Ziegler, Slava ;

Rauh, Daniel ;

Waldmann, Herbert .

NATURE CHEMISTRY, 2010, 2 (09) :735-740

[4] Total synthesis of marine natural products without using protecting groups [J].

Baran, Phil S. ;

Maimone, Thomas J. ;

Richter, Jeremy M. .

NATURE, 2007, 446 (7134) :404-408

[5] Emergence of diversity and stereochemical outcomes in the biosynthetic pathways of cyclobutane-centered marine alkaloid dimers [J].

Beniddir, Mehdi A. ;

Evanno, Laurent ;

Joseph, Delphine ;

Skiredj, Adam ;

Poupon, Erwan .

NATURAL PRODUCT REPORTS, 2016, 33 (07) :820-842

[6] Selective transition-metal-free vicinal cis-dihydroxylation of saturated hydrocarbons [J].

Bering, Luis ;

Antonchick, Andrey P. .

CHEMICAL SCIENCE, 2017, 8 (01) :452-457

[7] Synthesis of Sulfonimidamides from Sulfenamides via an Alkoxy-amino-λ6-sulfanenitrile Intermediate [J].

Briggs, Edward L. ;

Tota, Arianna ;

Colella, Marco ;

Degennaro, Leonardo ;

Luisi, Renzo ;

Bull, James A. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (40) :14303-14310

[8] One-Pot Synthesis of Aryl- and Alkyl S-Perfluoroalkylated NH-Sulfoximines from Sulfides [J].

Chaabouni, Slim ;

Lohier, Jean-Francois ;

Barthelemy, Anne-Laure ;

Glachet, Thomas ;

Anselmi, Elsa ;

Dagousset, Guillaume ;

Diter, Patrick ;

Pegot, Bruce ;

Magnier, Emmanuel ;

Reboul, Vincent .

CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (64) :17006-17010

[9] Enantioselective Total Synthesis of (+)-Psiguadial B [J].

Chapman, Lauren M. ;

Beck, Jordan C. ;

Wu, Linglin ;

Reisman, Sarah E. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (31) :9803-9806

[10] Hydrogen Bonding to Hexafluoroisopropanol Controls the Oxidative Strength of Hypervalent Iodine Reagents [J].

Colomer, Ignacio ;

Batchelor-McAuley, Christopher ;

Odell, Barbara ;

Donohoe, Timothy J. ;

Compton, Richard G. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (28) :8855-8861

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