Bifunctional squaramide‐catalysed enantioselective vinylogous Michael addition/cyclization cascade reaction of 4‐unsturated isoxazol‐5‐ones and α,α‐dicyanoalkenes

2021 ◽  
Author(s):  
Yu Wang ◽  
Cheng Niu ◽  
Donghua Xie ◽  
Da-Ming Du
Keyword(s):  
Michael Addition ◽  
Stereoselective Synthesis ◽  
Cascade Reaction ◽  
Cascade Process ◽  
Effective Strategy

An effective strategy for the stereoselective synthesis of spiro isoxazolone-cyclohexenimines was developed by bifunctional squaramide–catalysed vinylogous Michael addition/cyclization cascade reaction of 4-unsaturated isoxazol-5-ones and α,α-dicyanoalkenes. The atom-economical cascade process can...

scholarly journals Access to 6-hydroxy indolizines and related imidazo[1,5-a]pyridines through the SN2 substitution/condensation/tautomerization cascade process

RSC Advances ◽  
2021 ◽  
Vol 11 (41) ◽  
pp. 25624-25627
Author(s):  
Guiyun Duan ◽  
Hao Liu ◽  
Liqing Zhang ◽  
Chunhao Yuan ◽  
Yongchao Li ◽  
...  
Keyword(s):  
Cascade Reaction ◽  
Cascade Process

A simple and efficient cascade reaction was developed for the construction of hydroxy substituted indolizines from pyrrole-2-carbaldehydes and commercially available 4-halogenated acetoacetic esters.

Highly Cumulated Radical Cascade Reaction of aza-1,6-Enyenes: Stereoselective Synthesis of exo -Methylene Piperidines

2020 ◽  
Vol 2020 (11) ◽  
pp. 1700-1707
Author(s):  
Akio Kamimura ◽  
Tomoyuki Itaya ◽  
Tatsuro Yoshinaga ◽  
Ryo Nozawa ◽  
Takuji Kawamoto ◽  
...  
Keyword(s):  
Stereoselective Synthesis ◽  
Cascade Reaction ◽  
Radical Cascade

Uncatalyzed diastereoselective synthesis of alkyliminofurochromone-derived benzylmalononitriles via a three-component cascade reaction: competition between Diels–Alder cycloaddition and Michael addition

2021 ◽  
Author(s):  
Mohammad Bagher Teimouri ◽  
Zahra Mokhtare ◽  
Hamid Reza Khavasi
Keyword(s):  
Michael Addition ◽  
Heterocyclic Ring ◽  
Cascade Reaction ◽  
Diels Alder ◽  
Chemical Bonds ◽  
Diastereoselective Synthesis ◽  
Atom Economy ◽  
One Pot

Three new chemical bonds and three stereogenic centres and one heterocyclic ring were assembled stereoselectively in a convenient high atom-economy one-pot operation.

Stereoselective Synthesis of Diverse Lactones through a Cascade Reaction of Rhodium Carbenoids with Ketoacids

2018 ◽  
Vol 20 (23) ◽  
pp. 7585-7589 ◽  
Author(s):  
Nicholas P. Massaro ◽  
Joseph C. Stevens ◽  
Aayushi Chatterji ◽  
Indrajeet Sharma
Keyword(s):  
Stereoselective Synthesis ◽  
Cascade Reaction ◽  
Rhodium Carbenoids

Asymmetric synthesis of highly functionalized spirothiazolidinone tetrahydroquinolines via a squaramide-catalyzed cascade reaction

2018 ◽  
Vol 16 (48) ◽  
pp. 9390-9401 ◽  
Author(s):  
Yong-Xing Song ◽  
Da-Ming Du
Keyword(s):  
Asymmetric Synthesis ◽  
Michael Addition ◽  
Addition Reaction ◽  
Cascade Reaction ◽  
Michael Addition Reaction

A bifunctional squaramide-catalyzed asymmetric cascade aza-Michael/Michael addition reaction for the synthesis of chiral spirothiazolidinone tetrahydroquinolines with three contiguous stereocenters has been developed.

scholarly journals Stereodivergent assembly of tetrahydro-γ-carbolines via synergistic catalytic asymmetric cascade reaction

2019 ◽  
Vol 10 (1) ◽  
Author(s):  
Shi-Ming Xu ◽  
Liang Wei ◽  
Chong Shen ◽  
Lu Xiao ◽  
Hai-Yan Tao ◽  
...  
Keyword(s):  
Natural Products ◽  
Structural Unit ◽  
Indole Alkaloids ◽  
Catalyst System ◽  
Cascade Reaction ◽  
Vital Role ◽  
System Control ◽  
Cascade Process ◽  
Basic Structural Unit ◽  
Stereogenic Centers

AbstractEnantiomerically enriched indole-containing heterocycles play a vital role in bioscience, medicine, and chemistry. As one of the most attractive subtypes of indole alkaloids, highly substituted tetrahydro-γ-carbolines are the basic structural unit in many natural products and pharmaceuticals. However, the syntheses of tetrahydro-γ-carbolines with high functionalities from readily available reagents are significant challenging. In particular, the stereodivergent syntheses of tetrahydro-γ-carbolines containing multi-stereogenic centers remain quite difficult. Herein, we report an expedient and stereodivergent assembly of tetrahydro-γ-carbolines with remarkably high levels of stereoselective control in an efficient cascade process from aldimine esters and indolyl allylic carbonates via a synergistic Cu/Ir catalyst system. Control experiments-guided optimization of synergistic catalysts and mechanistic investigations reveal that a stereodivergent allylation reaction and a subsequent highly stereoselective iso-Pictet-Spengler cyclization are the key elements to success.

Stereoselective Synthesis of Bicyclic Pyrrolidines by a Rhodium-Catalyzed Cascade Process

2004 ◽  
Vol 43 (48) ◽  
pp. 6713-6716 ◽  
Author(s):  
Ming Yan ◽  
Neil Jacobsen ◽  
Wenhao Hu ◽  
Luisa S. Gronenberg ◽  
Michael P. Doyle ◽  
...  
Keyword(s):  
Stereoselective Synthesis ◽  
Cascade Process
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