Rhodium-catalysed alkoxylation/acetalization of diazo compounds: one-step synthesis of highly functionalised quaternary carbon centres

2015 ◽  
Vol 51 (77) ◽  
pp. 14505-14508 ◽  
Author(s):  
Jola Pospech ◽  
Alastair J. J. Lennox ◽  
Matthias Beller
Keyword(s):  
Diazo Compounds ◽  
Tandem Reaction ◽  
Quaternary Carbon ◽  
One Step

An intermolecular tandem reaction for the rapid build-up of densely functionalised α-alkoxy-β-oxo-esters has been developed.

Three-Component [1+1+1] Cyclopropanation with Ruthenium(II)

2018 ◽  
Author(s):  
Tanner C. Jankins ◽  
Robert R. Fayzullin ◽  
Eugene Khaskin
Keyword(s):  
Quaternary Carbon ◽  
Poor Control ◽  
One Step ◽  
Synthetic Routes ◽  
Mechanistic Investigations ◽  
Chiral Centers ◽  
Metal Catalyzed ◽  
The Right ◽  
Substituted Cyclopropanes

We report a one-step, Ru(II)-catalyzed cyclopropanation reaction that is conceptually different from the previously reported protocols that include Corey-Chaykovsky, Simmons-Smith, and metal catalyzed carbene attack on olefins. Under the current protocol, various alcohols are transformed into sulfone substituted cyclopropanes with excellent isolated yields and diastereoselectivities. This new reaction forms highly congested cyclopropane products with three new C–C bonds, three or two new chiral centers and one new quaternary carbon center. 22 examples of isolated substrates are given. Previously reported synthetic routes for similar substrates are all multi-step, linear routes that proceed with overall low yields and poor control of stereochemistry. Experimental mechanistic investigations suggest initial metal-catalyzed dehydrogenation of the alcohol substrate and catalyst independent stepwise attack of two equivalents of sulfone on the aldehyde under basic conditions. While the Ru(II) is only responsible for the initial dehydrogenation step, the rate of aldehyde formation is crucial to maintaining the right balance of intermediates needed to afford the cyclopropane product.

Catalytic Asymmetric Tandem Reaction of o-Alkynylbenzaldehydes, Amines, and Diazo Compounds

2021 ◽  
Author(s):  
Wei Wu ◽  
Na Liao ◽  
Qi Wei ◽  
Jiaying Huang ◽  
Qi Huang ◽  
...  
Keyword(s):  
Diazo Compounds ◽  
Tandem Reaction ◽  
Catalytic Asymmetric

Copper(I)-Catalyzed Tandem Synthesis of 2-Acylquinolines from 2-Ethynylanilines and Glyoxals

2021 ◽  
Author(s):  
Guanghui Wang ◽  
Jian Jia ◽  
Gang Liu ◽  
mingwu Yu ◽  
Xiaoxiao Chu ◽  
...  
Keyword(s):  
Tandem Reaction ◽  
One Step ◽  
Tandem Synthesis

An efficient one-step synthesis of 2-acylquinolines by a copper-catalyzed tandem reaction of 2-ethynylanilines with glyoxals in the presence of piperidine has been developed. This new protocol successfully avoids the multi-step...

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

2013 ◽  
Vol 85 (4) ◽  
pp. 741-753 ◽  
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.

Stereoselective synthesis of organosulfur compounds incorporating N-aromatic heterocyclic motifs and quaternary carbon centers via a sulfa-Michael triggered tandem reaction

2015 ◽  
Vol 51 (47) ◽  
pp. 9714-9717 ◽  
Author(s):  
Tianyou Qin ◽  
Lu Cheng ◽  
Sean Xiao-An Zhang ◽  
Weiwei Liao
Keyword(s):  
Michael Addition ◽  
Stereoselective Synthesis ◽  
Tandem Reaction ◽  
Organosulfur Compounds ◽  
The Novel ◽  
Quaternary Carbon ◽  
Carbon Centers ◽  
Aromatic Heterocyclic

The novel sulfa-Michael addition (SMA)-triggered tandem reaction was developed by combining a SMA reaction with a simultaneous rearomatization process.

A controlled selective synthesis of dihydropyrans through tandem reaction of alkynes with diazo compounds

2017 ◽  
Vol 53 (31) ◽  
pp. 4350-4353 ◽  
Author(s):  
Junxiang Min ◽  
Guangyang Xu ◽  
Jiangtao Sun
Keyword(s):  
Michael Addition ◽  
Diazo Compounds ◽  
Tandem Reaction ◽  
Controlled Synthesis ◽  
Selective Synthesis ◽  
Sequential Reaction

A controlled synthesis of dihydropyrans via sequential reaction of allenoate formation and intramolecular oxo-Michael addition has been achieved.

A rhodium-catalyzed tandem reaction of N-sulfonyl triazoles with indoles: access to indole-substituted indanones

2017 ◽  
Vol 53 (65) ◽  
pp. 9089-9092 ◽  
Author(s):  
Hao Yuan ◽  
Jianxian Gong ◽  
Zhen Yang
Keyword(s):  
Tandem Reaction ◽  
Quaternary Carbon ◽  
Carbon Centers

Rhodium(ii)-catalyzed tandem reaction of N-sulfonyl triazoles with indoles delivered structurally diverse indole-substituted indanones bearing vicinal quaternary carbon centers.

Sign in / Sign up

Export Citation Format

Share Document