Efficiently diastereoselective synthesis of functionalized hydro-carbazoles by base-mediated tandem annulation of 1-(2-amino-aryl)prop-2-en-1-ones and sulfur ylide

The base-promoted [3 + 3]/[1 + 4] tandem reaction of tosyl-protected o-amino α,β-unsaturated ketones and crotonate-derived sulfur ylide is developed for efficiently diastereoselective synthesis of functionalized hydrocarbazoles.

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The Diastereoselective Synthesis of Quaternary Substituted Thioindolines from Sulfur Ylide Intermediates

The Journal of Organic Chemistry ◽

10.1021/jo0482413 ◽

2005 ◽

Vol 70 (2) ◽

pp. 746-748 ◽

Cited By ~ 26

Author(s):

Abijah M. Nyong ◽

Jon D. Rainier

Keyword(s):

Diastereoselective Synthesis ◽

Sulfur Ylide

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Aziridinyl imines in organic synthesis: Development of tandem reaction strategies and application to total synthesis of natural products

Pure and Applied Chemistry ◽

10.1351/pac-con-12-10-01 ◽

2013 ◽

Vol 85 (4) ◽

pp. 741-753 ◽

Cited By ~ 11

Author(s):

Hee-Yoon Lee ◽

Seog-Beom Song ◽

Taek Kang ◽

Yoon Jung Kim ◽

Su Jeong Geum

Keyword(s):

Natural Products ◽

Total Synthesis ◽

Organic Synthesis ◽

Reactive Intermediates ◽

Diazo Compounds ◽

Tandem Reaction ◽

Cycloaddition Reactions ◽

Free Radical Reactions ◽

Sulfur Ylide ◽

Epoxide Formation

Aziridinyl imines are well-known carbene equivalents because they are precursors of diazo compounds from which reactive intermediates can be produced. These carbene equivalents can be utilized as zwitterionic species, diradicals, or 4π system for cycloaddition reactions. Thus, the intermediates derived from aziridinyl imines have been used in the sulfur-ylide-mediated epoxide formation, tandem free-radical reactions, or cyclopropanation reaction via carbene intermediates to form trimethylenemethane (TMM) diyls, which undergo [2 + 3] cycloaddition reactions to form cyclopentanoids. Diazo compounds generated from aziridinyl imines also react with allenes to form TMM diyls. This reaction was utilized in tandem cycloaddition reactions of linear substrates to form polyquinanes. These tandem reaction strategies were successfully applied to the total synthesis of various cyclopentanoid natural products.

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Environmentally benign access to isoindolinones: synthesis, separation and resource recycling

Green Chemistry ◽

10.1039/d0gc00957a ◽

2020 ◽

Vol 22 (9) ◽

pp. 2873-2878

Author(s):

Weiwei Guo ◽

Qi Zhang ◽

Yang Cao ◽

Kaihua Cai ◽

Shengyong Zhang ◽

...

Keyword(s):

Environmentally Benign ◽

Tandem Reaction ◽

Unsaturated Ketones ◽

Resource Recycling

We have developed a green and facile approach for the straightforward installation of isoindolinone skeletons via a tandem reaction of 2-cyanobenzaldehydes and α,β-unsaturated ketones/esters.

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Highly chemo- and diastereoselective synthesis of substituted tetrahydropyran-4-ones via organocatalytic oxa-Diels–Alder reactions of acyclic α,β-unsaturated ketones with aldehydes

Tetrahedron Letters ◽

10.1016/j.tetlet.2008.01.025 ◽

2008 ◽

Vol 49 (10) ◽

pp. 1631-1635 ◽

Cited By ~ 17

Author(s):

Liang-Qiu Lu ◽

Xiao-Ning Xing ◽

Xu-Fan Wang ◽

Zhi-Hui Ming ◽

Hong-Mei Wang ◽

...

Keyword(s):

Diels Alder ◽

Diastereoselective Synthesis ◽

Unsaturated Ketones

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Reactions of 2-hydroxyaryl-α,β-unsaturated ketones with dimethylsulfonium carbonylmethylides: a new and facile diastereoselective synthesis of 2,3-disubstituted dihydrobenzofurans

Tetrahedron ◽

10.1016/j.tet.2009.02.041 ◽

2009 ◽

Vol 65 (19) ◽

pp. 3918-3924 ◽

Cited By ~ 16

Author(s):

Sarika Malik ◽

Upender K. Nadir ◽

Pramod S. Pandey

Keyword(s):

Diastereoselective Synthesis ◽

Unsaturated Ketones

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Oxidative Asymmetric Formal Aza-Diels–Alder Reactions of Tetrahydro-β-carboline with Enones in the Synthesis of Indoloquinolizidine-2-ones

Molecules ◽

10.3390/molecules23092228 ◽

2018 ◽

Vol 23 (9) ◽

pp. 2228 ◽

Cited By ~ 2

Author(s):

Xiang Wu ◽

Shi-Bao Zhao ◽

Lang-Lang Zheng ◽

You-Gui Li

Keyword(s):

Oxidative Dehydrogenation ◽

Alder Reaction ◽

Diels Alder ◽

Diastereoselective Synthesis ◽

Butyl Hydroperoxide ◽

Unsaturated Ketones ◽

Tert Butyl ◽

Diels Alder Reaction ◽

Tert Butyl Hydroperoxide ◽

Reaction Proceeds

Ru-catalyzed tandem amine oxidative dehydrogenation/formal aza-Diels–Alder reaction for enantio- and diastereoselective synthesis of indoloquinolizidine-2-ones from tetrahydro-β-carbolines and α,β-unsaturated ketones is described. The reaction proceeds via tandem ruthenium-catalyzed amine dehydrogenation using tert-butyl hydroperoxide (TBHP) as the oxidant and a chiral thiourea-catalyzed formal aza-[4 + 2] cycloaddition, providing a step-economical strategy for the synthesis of these valuable heterocyclic products.

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