Literature DB >> 11041836

Dynamic thermodynamic resolution: control of enantioselectivity through diastereomeric equilibration.

P Beak1, D R Anderson, M D Curtis, J M Laumer, D J Pippel, G A Weisenburger.   

Abstract

A theoretical foundation, tools for recognition and control, and recent examples of a class of asymmetric transformation termed dynamic thermodynamic resolution are presented. Enantioselective reaction pathways that involve an induced diastereomeric equilibration to intermediates, which are configurationally stable on the time scale of a subsequent reaction, are illustrated. Dynamic thermodynamic resolution differs from the classic, well-documented pathways of kinetic resolution and dynamic kinetic resolution in that equilibration and resolution can be operative on one system in separate controllable steps. This approach offers a high level of flexibility and provides multiple opportunities for optimization of enantioselectivity.

Mesh:

Year:  2000        PMID: 11041836     DOI: 10.1021/ar000077s

Source DB:  PubMed          Journal:  Acc Chem Res        ISSN: 0001-4842            Impact factor:   22.384


  14 in total

Review 1.  Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds.

Authors:  Alan H Cherney; Nathaniel T Kadunce; Sarah E Reisman
Journal:  Chem Rev       Date:  2015-08-13       Impact factor: 60.622

2.  Do the terms "% ee" and "% de" make sense as expressions of stereoisomer composition or stereoselectivity?

Authors:  Robert E Gawley
Journal:  J Org Chem       Date:  2006-03-17       Impact factor: 4.354

3.  Overview of Carbanion Dynamics and Electrophilic Substitutions in Chiral Organolithium Compounds.

Authors:  Robert E Gawley
Journal:  Top Stereochem       Date:  2010-01-01

4.  Monitoring interconversion between stereochemical states in single chirality-transfer complexes on a platinum surface.

Authors:  Guillaume Goubert; Yi Dong; Michael N Groves; J-C Lemay; Bjørk Hammer; Peter H McBreen
Journal:  Nat Chem       Date:  2017-04-03       Impact factor: 24.427

5.  Diastereodivergent Synthesis of Chiral Tetrahydropyrrolodiazepinediones via a One-Pot Intramolecular aza-Michael/Lactamization Sequence.

Authors:  Spandan Chennamadhavuni; James S Panek; John A Porco; Lauren E Brown
Journal:  J Org Chem       Date:  2018-12-05       Impact factor: 4.354

6.  Synthetic applications and inversion dynamics of configurationally stable 2-lithio-2-arylpyrrolidines and -piperidines.

Authors:  Timothy K Beng; Jin Sun Woo; Robert E Gawley
Journal:  J Am Chem Soc       Date:  2012-08-27       Impact factor: 15.419

7.  Dynamics of catalytic resolution of 2-lithio-N-Boc-piperidine by ligand exchange.

Authors:  Timothy K Beng; William S Tyree; Trent Parker; Chicheung Su; Paul G Williard; Robert E Gawley
Journal:  J Am Chem Soc       Date:  2012-09-25       Impact factor: 15.419

8.  The barrier to enantiomerization and dynamic resolution of N-Boc-2-lithiopiperidine and the effect of TMEDA.

Authors:  Iain Coldham; Daniele Leonori; Timothy K Beng; Robert E Gawley
Journal:  Chem Commun (Camb)       Date:  2009-08-06       Impact factor: 6.222

9.  Enantiomerization dynamics and a catalytic dynamic resolution of N-trimethylallyl-2-lithiopyrrolidine.

Authors:  Timothy K Beng; Taher I Yousaf; Iain Coldham; Robert E Gawley
Journal:  J Am Chem Soc       Date:  2009-05-27       Impact factor: 15.419

10.  The barrier to enantiomerization of N-Boc-2-lithiopyrrolidine: the effect of chiral and achiral diamines.

Authors:  Taher I Yousaf; Roger L Williams; Iain Coldham; Robert E Gawley
Journal:  Chem Commun (Camb)       Date:  2008-01-07       Impact factor: 6.222

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