Literature DB >> 18512868

De-racemization of enantiomers versus de-epimerization of diastereomers--classification of dynamic kinetic asymmetric transformations (DYKAT).

Johannes Steinreiber1, Kurt Faber, Herfried Griengl.   

Abstract

The isolation of single stereoisomers from a racemic (or diastereomeric) mixture by enzymatic or chemical resolution techniques goes in hand with the disposal of 50% (racemate) or more (diastereomeric mixtures) of the "undesired" substrate isomer(s). In order to circumvent this drawback, dynamic systems have been developed for the de-racemization of enantiomers and the de-epimerizations of diastereomers. Key strategies within this area are discussed and are classified according to their underlying kinetics, that is, dynamic kinetic resolution (DKR), dynamic kinetic asymmetric transformations (DYKAT), and hybrids between both of them. Finally, two novel types of DYKAT are defined.

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Year:  2008        PMID: 18512868     DOI: 10.1002/chem.200701643

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  22 in total

1.  Dynamic kinetic resolution of biaryl atropisomers via peptide-catalyzed asymmetric bromination.

Authors:  Jeffrey L Gustafson; Daniel Lim; Scott J Miller
Journal:  Science       Date:  2010-06-04       Impact factor: 47.728

2.  Organoselenium-catalyzed enantioselective syn-dichlorination of unbiased alkenes.

Authors:  Bradley B Gilbert; Stanley T-C Eey; Pavel Ryabchuk; Olivia Garry; Scott E Denmark
Journal:  Tetrahedron       Date:  2019-06-01       Impact factor: 2.457

3.  Single-operation deracemization of 3H-indolines and tetrahydroquinolines enabled by phase separation.

Authors:  Aaron D Lackner; Andrew V Samant; F Dean Toste
Journal:  J Am Chem Soc       Date:  2013-09-11       Impact factor: 15.419

4.  "It's a (Kinetic) Trap!" - Selectively Differentiating Allylic Azide Isomers.

Authors:  Joseph J Topczewski; Matthew R Porter
Journal:  Synlett       Date:  2018-07       Impact factor: 2.454

5.  Diametric stereocontrol in dynamic catalytic reduction of racemic acyl phosphonates: divergence from α-keto ester congeners.

Authors:  Michael T Corbett; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2013-01-08       Impact factor: 15.419

6.  Caution in the Use of Nonlinear Effects as a Mechanistic Tool for Catalytic Enantioconvergent Reactions: Intrinsic Negative Nonlinear Effects in the Absence of Higher-Order Species.

Authors:  Marcin Kalek; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2017-03-09       Impact factor: 15.419

7.  Enantioselective Diels-Alder-lactamization organocascades employing a furan-based diene.

Authors:  Mikail E Abbasov; Brandi M Hudson; Weixu Kong; Dean J Tantillo; Daniel Romo
Journal:  Org Biomol Chem       Date:  2017-04-11       Impact factor: 3.876

8.  Development of dynamic kinetic resolution on large scale for (±)-1-phenylethylamine.

Authors:  Lisa K Thalén; Jan-E Bäckvall
Journal:  Beilstein J Org Chem       Date:  2010-09-13       Impact factor: 2.883

Review 9.  Catalytic, Stereoselective Dihalogenation of Alkenes: Challenges and Opportunities.

Authors:  Alexander J Cresswell; Stanley T-C Eey; Scott E Denmark
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-02       Impact factor: 15.336

10.  Dynamic kinetic asymmetric transformations of β-stereogenic α-ketoesters by direct aldolization.

Authors:  Michael T Corbett; Jeffrey S Johnson
Journal:  Angew Chem Int Ed Engl       Date:  2013-11-12       Impact factor: 15.336

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