(4+3)-Cycloaddition of Donor-Acceptor Cyclopropanes with Thiochalcones: A Diastereoselective Access to Tetrahydrothiepines

A general approach is described for the formation of tetrahydrothiepines using donor-acceptor cyclopropanes. Thiochalcones, functioning as sulfur-containing four-atom building blocks, were reacted in a Lewis-acid-catalyzed formal (4+3)-cycloaddition reaction with donor-acceptor cyclopropanes as three-atom building blocks. Under mild conditions various tetrahydrothiepines were synthesized in good yields in a stereosepecific reaction with high functional group tolerance.

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(4+3)-Cycloaddition of Donor-Acceptor Cyclopropanes with Thiochalcones: A Diastereoselective Access to Tetrahydrothiepines

10.26434/chemrxiv.9955202.v1 ◽

2019 ◽

Author(s):

André U. Augustin ◽

J. Luca Merz ◽

Peter G. Jones ◽

Grzegorz Mloston ◽

Daniel Werz

Keyword(s):

Lewis Acid ◽

Functional Group ◽

Cycloaddition Reaction ◽

Building Blocks ◽

Mild Conditions ◽

Donor Acceptor ◽

Acid Catalyzed ◽

Sulfur Containing

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Lewis Acid Catalyzed [3+2] Annulations of γ-Butyrolactam-Fused Donor-Acceptor Cyclopropanes with Aromatic Aldehydes and Aldimines

European Journal of Organic Chemistry ◽

10.1002/ejoc.202000818 ◽

2020 ◽

Cited By ~ 1

Author(s):

Peiying Su ◽

Huimin Li ◽

Wenlong Chen ◽

Gen Luo ◽

Gaosheng Yang ◽

...

Keyword(s):

Lewis Acid ◽

Aromatic Aldehydes ◽

Donor Acceptor ◽

Acid Catalyzed

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Lewis‐Acid‐Catalyzed (3+2)‐Cycloadditions of Donor‐Acceptor Cyclopropanes with Thioketenes

European Journal of Organic Chemistry ◽

10.1002/ejoc.202100879 ◽

2021 ◽

Author(s):

Grzegorz Mlostoń ◽

Mateusz Kowalczyk ◽

André U. Augustin ◽

Peter G. Jones ◽

Daniel B. Werz

Keyword(s):

Lewis Acid ◽

Donor Acceptor ◽

Acid Catalyzed

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Synthesis of 4-heterocyclyl-hexahydro-8-methoxyfuro[3,2-c]quinolines by Lewis acid catalyzed [4 + 2]cycloaddition reaction

Journal of Heterocyclic Chemistry ◽

10.1002/jhet.5570230138 ◽

1986 ◽

Vol 23 (1) ◽

pp. 185-187 ◽

Cited By ~ 17

Author(s):

Tetsuji Kametani ◽

Hiroko Furuyama ◽

Yukari Fukuoka ◽

Hajime Takeda ◽

Yukio Suzuki ◽

...

Keyword(s):

Lewis Acid ◽

Cycloaddition Reaction ◽

Acid Catalyzed

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Scope and Mechanism for Lewis Acid-Catalyzed Cycloadditions of Aldehydes and Donor−Acceptor Cyclopropanes: Evidence for a Stereospecific Intimate Ion Pair Pathway

Journal of the American Chemical Society ◽

10.1021/ja8015928 ◽

2008 ◽

Vol 130 (27) ◽

pp. 8642-8650 ◽

Cited By ~ 252

Author(s):

Patrick D. Pohlhaus ◽

Shanina D. Sanders ◽

Andrew T. Parsons ◽

Wei Li ◽

Jeffrey S. Johnson

Keyword(s):

Lewis Acid ◽

Ion Pair ◽

Donor Acceptor ◽

Acid Catalyzed

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Lewis Acid Catalyzed Stereoselective Dearomative Coupling of Indolylboron Ate Complexes with Donor-Acceptor Cyclopropanes and Alkyl Halides

Angewandte Chemie ◽

10.1002/ange.201711923 ◽

2018 ◽

Vol 130 (15) ◽

pp. 4117-4121 ◽

Cited By ~ 28

Author(s):

Saikat Das ◽

Constantin G. Daniliuc ◽

Armido Studer

Keyword(s):

Lewis Acid ◽

Alkyl Halides ◽

Donor Acceptor ◽

Acid Catalyzed

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Lewis Acid Catalyzed [3+3] Annulation of Donor-Acceptor Cyclopropanes with γ-Hydroxyenones: Access to Highly Functionalized Tetrahydropyrans

European Journal of Organic Chemistry ◽

10.1002/ejoc.201601305 ◽

2017 ◽

Vol 2017 (3) ◽

pp. 534-537 ◽

Cited By ~ 22

Author(s):

Keshab Mondal ◽

Subhas Chandra Pan

Keyword(s):

Lewis Acid ◽

Donor Acceptor ◽

Acid Catalyzed

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Efficient Synthesis of Diarylmethylamines via Lewis Acid Catalyzed Friedel–Crafts Reactions of Donor–Acceptor Aziridines with N,N-Dialkylanilines

Synthesis ◽

10.1055/s-0039-1690731 ◽

2019 ◽

Vol 52 (02) ◽

pp. 281-289

Author(s):

Yerin Kim ◽

Yong Il Kwon ◽

Sung-Gon Kim

Keyword(s):

Lewis Acid ◽

Efficient Synthesis ◽

Broad Scope ◽

Donor Acceptor ◽

Acid Catalyzed ◽

High Yields

A method for efficient and mild synthesis of diarylmethylamine scaffold, via Lewis acid catalyzed Friedel–Crafts reaction of donor–acceptor aziridines with N,N-dialkylanilines to afford a biologically important diarylmethylamine derivatives in high yields (up to 88%), is presented. This reaction is suitable for the synthesis of various diarylmethylamine derivatives and has a broad scope for electron-rich arenes, including dimethoxybenzene.

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