scholarly journals Highly Efficient Kinetic Resolution of Aryl-Alkenyl Alcohols by Ru-Catalyzed Hydrogen Transfer

Molecules ◽  
2021 ◽  
Vol 26 (24) ◽  
pp. 7475
Author(s):  
Yipeng You ◽  
Ming Yu Jin ◽  
Guanyu Tao ◽  
Xiangyou Xing
Keyword(s):  
Organic Synthesis ◽  
Hydrogen Transfer ◽  
Kinetic Resolution ◽  
Asymmetric Reduction ◽  
Building Blocks ◽  
Enantioselective Synthesis ◽  
Allylic Alcohols ◽  
Secondary Alcohols ◽  
Highly Efficient ◽  
Reduction Of Ketones

No matter through asymmetric reduction of ketones or kinetic resolution of secondary alcohols, enantioselective synthesis of the corresponding secondary alcohols is challenging when the two groups attached to the prochiral or chiral centers are spatially or electronically similar. For examples, dialkyl (sp3 vs. sp3), diaryl (sp2 vs. sp2), and aryl-alkenyl (sp2 vs. sp2) alcohols are difficult to produce with high enantioselectivities. By exploiting our recently developed Ru-catalysts of minimal stereogenicity, we reported herein a highly efficient kinetic resolution of aryl-alkenyl alcohols through hydrogen transfer. This method enabled such versatile chiral building blocks for organic synthesis as allylic alcohols, to be readily accessed with excellent enantiomeric excesses at practically useful conversions.

ChemInform Abstract: Kinetic Resolution of Racemic Secondary Alcohols by Ru(II)-Catalyzed Hydrogen Transfer.

ChemInform ◽  
2010 ◽  
Vol 28 (19) ◽  
pp. no-no
Author(s):  
S. HASHIGUCHI ◽  
A. FUJII ◽  
K.-J. HAACK ◽  
K. MATSUMURA ◽  
T. IKARIYA ◽  
...  
Keyword(s):  
Hydrogen Transfer ◽  
Kinetic Resolution ◽  
Secondary Alcohols

Use of enzymes as catalysts to promote key transformations in organic synthesis

1989 ◽  
Vol 324 (1224) ◽  
pp. 577-587 ◽  
Keyword(s):  
Organic Synthesis ◽  
Large Scale ◽  
Immobilized Enzymes ◽  
Building Blocks ◽  
Optically Active ◽  
The Past ◽  
Small Proteins ◽  
Areas Of Interest ◽  
Oxidation Of Benzene ◽  
Reduction Of Ketones

The field of biotransformations has developed rapidly over the past eight years. The use of esterases and lipases is now widespread; these enzymes are of particular importance in the production of optically active building blocks for organic synthesis as well as in large-scale processes involving the transesterification of fats. The latter area (i.e. the catalysis of esterification processes) has stimulated research into the properties of immobilized enzymes and the use of enzymes in low-water systems. In related work, enzymes have been used for the preparation of peptides and small proteins. Redox enzymes have been investigated extensively, particularly with regard to the stereocontrolled reduction of ketones to secondary alcohols. The methods for using commercially available enzymes of this type have become increasingly ‘userfriendly’. The controlled oxidation of hydrocarbon units is another area that has deserved increased attention. For example, oxidation of benzene and simple derivatives by Pseudomonas sp. has been researched by a number of U.K. groups. These recent advances in enzyme-catalysed reactions (using both whole-cell systems and partly purified protein) for the transformation of unnatural substrates is discussed and some areas of interest for the future are outlined.

Kinetic Resolution of Racemic Secondary Alcohols by RuII-Catalyzed Hydrogen Transfer

1997 ◽  
Vol 36 (3) ◽  
pp. 288-290 ◽  
Author(s):  
Shohei Hashiguchi ◽  
Akio Fujii ◽  
Karl-Josef Haack ◽  
Kazuhiko Matsumura ◽  
Takao Ikariya ◽  
...  
Keyword(s):  
Hydrogen Transfer ◽  
Kinetic Resolution ◽  
Secondary Alcohols

Gold(i)-catalyzed enantioselective synthesis of polycyclic indoline skeletons and enantiomerically enriched β-substituted tryptamine-allenes by kinetic resolution

2019 ◽  
Vol 55 (29) ◽  
pp. 4210-4213 ◽  
Author(s):  
Yan-Yan Zhang ◽  
Yin Wei ◽  
Min Shi
Keyword(s):  
Kinetic Resolution ◽  
Enantioselective Synthesis ◽  
Highly Efficient

We have developed a gold(i)-catalyzed highly efficient kinetic resolution of indole–allene derivatives, providing polycyclic indoline skeletons in good yields with high regio- and diastereoselectivities and enantioselectivities.

Reduction of Oximes and Hydrazones: Asymmetric and Diastereoselective Approaches

2021 ◽  
Vol 25 ◽  
Author(s):  
João L. P. Ribeiro ◽  
Cláudia Alves ◽  
Ana L. Cardoso ◽  
Susana M. M. Lopes ◽  
Teresa M. V. D. Pinho e Melo
Keyword(s):  
Organic Synthesis ◽  
Asymmetric Reduction ◽  
Building Blocks ◽  
Electrochemical Reactions ◽  
Chiral Amines ◽  
Diastereoselective Reduction ◽  
Metal Catalyzed ◽  
Made In

: The asymmetric reduction of oximes and hydrazones is an attractive and versatile strategy for the synthesis of chiral amines, which are valuable building blocks in organic synthesis. This review summarizes the relevant developments made in the last decade on the enantioselective and diastereoselective reduction of oximes and hydrazones involving metal-catalyzed hydrogenation/hydrogenolysis reactions, hydride donor reactions, and electrochemical reactions.

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