Literature DB >> 33716355

Dynamic Covalent Kinetic Resolution.

Yan Zhang1, Yang Zhang2, Olof Ramström3,4.   

Abstract

Implemented with the highly efficient concept of Dynamic Kinetic Resolution (DKR), dynamic covalent chemistry can be a useful strategy for the synthesis of enantioenriched compounds. This gives rise to dynamic covalent kinetic resolution (DCKR), a subset of DKR that over the last decades has emerged as increasingly fruitful, with many applications in asymmetric synthesis and catalysis. All DKR protocols are composed of two important parts: substrate racemization and asymmetric transformation, which can lead to yields of >50% with good enantiomeric excesses (ee) of the products. In DCKR systems, by utilizing reversible covalent reactions as the racemization strategy, the substrate enantiomers can be easily interconverted without the presence of any racemase or transition metal catalyst. Enzymes or other chiral catalysts can then be adopted for the resolution step, leading to products with high enantiopurities. This tutorial review focuses on the development of DCKR systems, based on different reversible reactions, and their applications in asymmetric synthesis.

Entities:  

Keywords:  Asymmetric synthesis; Dynamic covalent chemistry; Dynamic kinetic resolution; Enzymatic catalysis; Organocatalysis

Year:  2019        PMID: 33716355      PMCID: PMC7953846          DOI: 10.1080/01614940.2019.1664031

Source DB:  PubMed          Journal:  Catal Rev Sci Eng        ISSN: 0161-4940            Impact factor:   20.217


  36 in total

Review 1.  Enzyme catalysed deracemisation and dynamic kinetic resolution reactions.

Authors:  Nicholas J Turner
Journal:  Curr Opin Chem Biol       Date:  2004-04       Impact factor: 8.822

2.  Dynamic asymmetric hemithioacetal transformation by lipase-catalyzed γ-lactonization: in situ tandem formation of 1,3-oxathiolan-5-one derivatives.

Authors:  Morakot Sakulsombat; Yan Zhang; Olof Ramström
Journal:  Chemistry       Date:  2012-04-04       Impact factor: 5.236

3.  Dynamic combinatorial resolution: direct asymmetric lipase-mediated screening of a dynamic nitroaldol library.

Authors:  Pornrapee Vongvilai; Marcus Angelin; Rikard Larsson; Olof Ramström
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

Review 4.  Deracemisation methods.

Authors:  Nicholas J Turner
Journal:  Curr Opin Chem Biol       Date:  2010-01-13       Impact factor: 8.822

5.  A highly diastereoselective and enantioselective synthesis of polysubstituted pyrrolidines via an organocatalytic dynamic kinetic resolution cascade.

Authors:  Tao Cheng; Sixuan Meng; Yong Huang
Journal:  Org Lett       Date:  2013-04-08       Impact factor: 6.005

Review 6.  Asymmetric Synthesis of Secondary and Tertiary Boronic Esters.

Authors:  Beatrice S L Collins; Claire M Wilson; Eddie L Myers; Varinder K Aggarwal
Journal:  Angew Chem Int Ed Engl       Date:  2017-08-09       Impact factor: 15.336

7.  Disulfide exchange: exposing supramolecular reactivity through dynamic covalent chemistry.

Authors:  Samuel P Black; Jeremy K M Sanders; Artur R Stefankiewicz
Journal:  Chem Soc Rev       Date:  2014-03-21       Impact factor: 54.564

8.  Asymmetric synthesis of trisubstituted tetrahydrothiophenes bearing a quaternary stereocenter via double Michael reaction involving dynamic kinetic resolution.

Authors:  Sara Meninno; Gianluca Croce; Alessandra Lattanzi
Journal:  Org Lett       Date:  2013-06-20       Impact factor: 6.005

Review 9.  Chemoenzymatic dynamic kinetic resolution: a powerful tool for the preparation of enantiomerically pure alcohols and amines.

Authors:  Oscar Verho; Jan-E Bäckvall
Journal:  J Am Chem Soc       Date:  2015-03-19       Impact factor: 15.419

10.  Asymmetric Synthesis of Substituted Thiolanes through Domino Thia-Michael-Henry Dynamic Covalent Systemic Resolution using Lipase Catalysis.

Authors:  Yan Zhang; Pornrapee Vongvilai; Morakot Sakulsombat; Andreas Fischer; Olof Ramström
Journal:  Adv Synth Catal       Date:  2014-03-03       Impact factor: 5.837

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