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

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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ChemInform Abstract: Highly Chemo- and Diastereoselective Synthesis of Substituted Tetrahydropyran-4-ones via Organocatalytic oxa-Diels-Alder Reactions of Acyclic α,β-Unsaturated Ketones with Aldehydes.

ChemInform ◽

10.1002/chin.200825135 ◽

2008 ◽

Vol 39 (25) ◽

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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Diastereoselective synthesis of diverse 3,2′-pyrrolidinyl bispirooxindoles via 1,3-dipolar cycloaddition reactions of azomethine ylides with exocyclic α,β-unsaturated ketones and in silico studies for prediction of bioactivity

Synthetic Communications ◽

10.1080/00397911.2018.1560472 ◽

2019 ◽

Vol 49 (3) ◽

pp. 444-455 ◽

Cited By ~ 1

Author(s):

Kartik Dutta ◽

Mukesh Kumar ◽

Sunil K. Ghosh ◽

Amit Das ◽

Raghunath Chowdhury

Keyword(s):

In Silico ◽

Azomethine Ylides ◽

Dipolar Cycloaddition ◽

Cycloaddition Reactions ◽

Diastereoselective Synthesis ◽

Unsaturated Ketones ◽

In Silico Studies

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ChemInform Abstract: Reactions of 2-Hydroxyaryl-α,β-Unsaturated Ketones with Dimethylsulfonium Carbonylmethylides: A New and Facile Diastereoselective Synthesis of 2,3-Disubstituted Dihydrobenzofurans.

ChemInform ◽

10.1002/chin.200934106 ◽

2009 ◽

Vol 40 (34) ◽

Author(s):

Sarika Malik ◽

Upender K. Nadir ◽

Pramod S. Pandey

Keyword(s):

Diastereoselective Synthesis ◽

Unsaturated Ketones

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Facile separation catalyst system: direct diastereoselective synthesis of (E)-α,β-unsaturated ketones catalyzed by an air-stable Lewis acidic/basic bifunctional organobismuth complex in ionic liquids

Green Chemistry ◽

10.1039/c004940a ◽

2010 ◽

Vol 12 (10) ◽

pp. 1767 ◽

Cited By ~ 30

Author(s):

Renhua Qiu ◽

Yimiao Qiu ◽

Shuangfeng Yin ◽

Xingxing Song ◽

Zhengong Meng ◽

...

Keyword(s):

Ionic Liquids ◽

Catalyst System ◽

Diastereoselective Synthesis ◽

Unsaturated Ketones

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Diastereoselective synthesis of functionalized tetrahydro-γ-carbolines via a [3 + 3] cycloaddition of 2,2′-diester aziridines with β-(indol-2-yl)-α,β-unsaturated ketones

Chinese Chemical Letters ◽

10.1016/j.cclet.2019.09.002 ◽

2020 ◽

Vol 31 (5) ◽

pp. 1293-1296 ◽

Cited By ~ 2

Author(s):

Xuejie Zou ◽

Yangzi Liu ◽

Shaojing Shang ◽

Wulin Yang ◽

Weiping Deng

Keyword(s):

Diastereoselective Synthesis ◽

Unsaturated Ketones

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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

Organic Chemistry Frontiers ◽

10.1039/d0qo00423e ◽

2020 ◽

Vol 7 (12) ◽

pp. 1469-1473 ◽

Cited By ~ 1

Author(s):

Chengyuan Wang ◽

Jiong Zhang ◽

Zheyuan Wang ◽

Xin-Ping Hui

Keyword(s):

Tandem Reaction ◽

Diastereoselective Synthesis ◽

Unsaturated Ketones ◽

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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