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

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.

scholarly journals Diazo Compounds-Involved Catalytic Asymmetric Multicomponent Reactions

2014 ◽  
Vol 34 (7) ◽  
pp. 1268 ◽  
Author(s):  
Min Tang ◽  
Dong Xing ◽  
Maoqiang Cai ◽  
Wenhao Hu
Keyword(s):  
Multicomponent Reactions ◽  
Diazo Compounds ◽  
Catalytic Asymmetric

Catalytic asymmetric trifluoromethylthiolation of carbonyl compounds via a diastereo and enantioselective Cu-catalyzed tandem reaction

2018 ◽  
Vol 54 (36) ◽  
pp. 4581-4584 ◽  
Author(s):  
Ming Yu Jin ◽  
Juncheng Li ◽  
Renke Huang ◽  
Yuxuan Zhou ◽  
Lung Wa Chung ◽  
...  
Keyword(s):  
Carbonyl Compounds ◽  
Tandem Reaction ◽  
Catalytic Asymmetric

The tandem reaction realizes the asymmetric integration of –SCF3 group to carbonyl compounds, establishing the chiral tertiary α-carbon center and affording the α-SCF3-β-substituted carbonyl compounds in 50–92% yields with up to 20 : 1 dr and 96% ee.

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.

Bimetallic Catalytic Asymmetric Tandem Reaction of β‐Alkynyl Ketones to Synthesize 6,6‐Spiroketals

2019 ◽  
Vol 58 (12) ◽  
pp. 4017-4021 ◽  
Author(s):  
Shulin Ge ◽  
Weidi Cao ◽  
Tengfei Kang ◽  
Bowen Hu ◽  
Hang Zhang ◽  
...  
Keyword(s):  
Tandem Reaction ◽  
Catalytic Asymmetric

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.

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