scholarly journals Chirality transfer in metal-catalysed intermolecular addition reactions involving allenes

2016 ◽  
Vol 3 (9) ◽  
pp. 1186-1204 ◽  
Author(s):  
José Miguel Alonso ◽  
María Teresa Quirós ◽  
María Paz Muñoz
Keyword(s):  
Asymmetric Catalysis ◽  
Addition Reactions ◽  
Chirality Transfer

This review covers chirality transfer in metal-catalysed intermolecular addition reactions involving allenes, including axial-to-central chirality transfer, asymmetric catalysis and racemization.

ChemInform Abstract: Chirality Transfer in Metal-Catalyzed Intermolecular Addition Reactions Involving Allenes

ChemInform ◽  
2016 ◽  
Vol 47 (46) ◽  
Author(s):  
Jose Miguel Alonso ◽  
Maria Teresa Quiros ◽  
Maria Paz Munoz
Keyword(s):  
Addition Reactions ◽  
Chirality Transfer ◽  
Metal Catalyzed

scholarly journals Chiral Diamine in Small Molecule Biomimetic Asymmetric Catalysis

2021 ◽  
Author(s):  
Fanyun Zeng ◽  
Chen Chen ◽  
Liu Liu ◽  
Yifan Li ◽  
Bo Li ◽  
...  
Keyword(s):  
Asymmetric Catalysis ◽  
Enzymatic Reaction ◽  
Addition Reactions ◽  
Broad Application ◽  
Design And Synthesis ◽  
Chiral Diamine ◽  
Commodity Chemicals ◽  
Great Progress ◽  
Further Development ◽  
Environmentally Friendly Approach

Enzymatic reaction, as an environmentally friendly approach, has made great progress producing commodity chemicals comparing to the conventional metallo/organo catalysis. However, the reaction compatibility is not satisfactory. The development of biomimetic catalysis balancing both strategies for the green and broad application in synthesis is desirable. Here, we report the design and synthesis of a chiral diamine catalyst fulfilling this requirement. Asymmetric addition reactions using this ligand in water were demonstrated and the corresponding products were produced in excellent yields and enantiomeric ratios. This pluripotent ligand has also shown good reactivity/enantioselectivity on a number of representative reactions in both green and organic solvents. We anticipate that the ligand would allow further development of other catalysts for important yet challenging green stereoselective transformations.

A Planar-Chiral Pillar[5]arene-Based Monophosphine Ligand with Induced Chirality at the Biaryl Axis

Synlett ◽  
2018 ◽  
Vol 29 (16) ◽  
pp. 2167-2170 ◽  
Author(s):  
Yuuya Nagata ◽  
Tomoki Ogoshi ◽  
Michinori Suginome ◽  
Yasuo Shimada ◽  
Tsuyoshi Nishikawa ◽  
...  
Keyword(s):  
Single Crystal ◽  
Diffraction Analysis ◽  
Asymmetric Catalysis ◽  
Cd Spectroscopy ◽  
Asymmetric Reactions ◽  
Side Chains ◽  
Chiral Ligand ◽  
X Ray Diffraction ◽  
Chirality Transfer ◽  
X Ray

A planar-chiral pillar[5]arene with cyclohexylmethoxy side chains and a pendant diphenylphosphine was prepared and used as a chiral ligand in asymmetric reactions. Chirality transfer from the planar-chiral pillar[5]arene scaffold to the chiral biaryl moiety was demonstrated by circular dichroism (CD) spectroscopy, single-crystal X-ray diffraction analysis, and asymmetric catalysis.

scholarly journals Evaluation of a chiral cubane-based Schiff base ligand in asymmetric catalysis reactions

2012 ◽  
Vol 8 ◽  
pp. 1814-1818 ◽  
Author(s):  
Kyle F Biegasiewicz ◽  
Michelle L Ingalsbe ◽  
Jeffrey D St. Denis ◽  
James L Gleason ◽  
Junming Ho ◽  
...  
Keyword(s):  
Schiff Base ◽  
Asymmetric Catalysis ◽  
Schiff Base Ligand ◽  
Membered Ring ◽  
Addition Reactions ◽  
Henry Reaction ◽  
Organic Transformations ◽  
Computational Evaluation ◽  
Copper Center ◽  
B3lyp Calculations

Recently, a novel chiral cubane-based Schiff base ligand was reported to yield modest enantioselectivity in the Henry reaction. To further explore the utility of this ligand in other asymmetric organic transformations, we evaluated its stereoselectivity in cyclopropanation and Michael addition reactions. Although there was no increase in stereocontrol, upon computational evaluation using both M06L and B3LYP calculations, it was revealed that a pseudo six-membered ring exists, through H-bonding of a cubyl hydrogen to the copper core. This decreases the steric bulk above the copper center and limits the asymmetric control with this ligand.

scholarly journals Tuning organic crystal chirality by the molar masses of tailored polymeric additives

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Xichong Ye ◽  
Bowen Li ◽  
Zhaoxu Wang ◽  
Jing Li ◽  
Jie Zhang ◽  
...  
Keyword(s):  
Asymmetric Catalysis ◽  
Crystal Engineering ◽  
Building Blocks ◽  
Oriented Attachment ◽  
Organic Crystals ◽  
Chirality Transfer ◽  
Precise Control ◽  
Polymeric Additives ◽  
Scope Of Application ◽  
Chiral Crystals

AbstractHierarchically ordered chiral crystals have attracted intense research efforts for their huge potential in optical devices, asymmetric catalysis and pharmaceutical crystal engineering. Major barriers to the application have been the use of costly enantiomerically pure building blocks and the difficulty in precise control of chirality transfer from molecular to macroscopic level. Herein, we describe a strategy that offers not only the preferred formation of one enantiomorph from racemic solution but also the subsequent enantiomer-specific oriented attachment of this enantiomorph by balancing stereoselective and non-stereoselective interactions. It is demonstrated by on-demand switching the sign of fan-shaped crystal aggregates and the configuration of their components only by changing the molar mass of tailored polymeric additives. Owing to the simplicity and wide scope of application, this methodology opens an immediate opportunity for facile and efficient fabrication of one-handed macroscopic aggregates of homochiral organic crystals from racemic starting materials.

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