Literature DB >> 12491751

Parallel kinetic resolution of racemic mixtures: a new strategy for the preparation of enantiopure compounds?

Juan R Dehli1, Vicente Gotor.   

Abstract

Kinetic resolution of racemic mixtures is a well-established methodology for the preparation of optically active compounds. However, excellent enantioselectivities are required to obtain them in enantiopure form, due to the decrease in ee when conversion values are close to 50%. To overcome this limitation, a parallel (asymmetric) reaction can remove the disfavored enantiomer. In this review, several examples of this strategy showing its wide range of applicability are described, as well as their mathematical treatment and some new applications in combinatorial chemistry.

Year:  2002        PMID： 12491751     DOI： 10.1039/b205280f

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN： 0306-0012            Impact factor:   54.564


  13 in total

1.  Enantioselective photocycloaddition of 3-hydroxyflavones: total syntheses and absolute configuration assignments of (+)-ponapensin and (+)-elliptifoline.

Authors:  Neil J Lajkiewicz; Stéphane P Roche; Baudouin Gerard; John A Porco
Journal:  J Am Chem Soc       Date:  2012-07-25       Impact factor: 15.419

2.  Catalytic parallel kinetic resolution under homogeneous conditions.

Authors:  Trisha A Duffey; James A Mackay; Edwin Vedejs
Journal:  J Org Chem       Date:  2010-07-16       Impact factor: 4.354

3.  Divergent Stereoselectivity in Phosphothreonine (pThr)-Catalyzed Reductive Aminations of 3-Amidocyclohexanones.

Authors:  Christopher R Shugrue; Aaron L Featherston; Rachel M Lackner; Angela Lin; Scott J Miller
Journal:  J Org Chem       Date:  2018-04-05       Impact factor: 4.354

4.  Organocatalytic enantioselective synthesis of both diastereomers of alpha-hydroxyphosphinates.

Authors:  Sampak Samanta; Sandun Perera; Cong-Gui Zhao
Journal:  J Org Chem       Date:  2010-02-19       Impact factor: 4.354

5.  Zr[bis(salicylidene)ethylenediaminato]-mediated Baeyer-Villiger oxidation: stereospecific synthesis of abnormal and normal lactones.

Authors:  Akira Watanabe; Tatsuya Uchida; Ryo Irie; Tsutomu Katsuki
Journal:  Proc Natl Acad Sci U S A       Date:  2004-04-08       Impact factor: 11.205

6.  Divergent outcomes of carbene transfer reactions from dirhodium- and copper-based catalysts separately or in combination.

Authors:  Xinfang Xu; Wen-Hao Hu; Peter Y Zavalij; Michael P Doyle
Journal:  Angew Chem Int Ed Engl       Date:  2011-10-06       Impact factor: 15.336

7.  Parallel kinetic resolution approach to the cyathane and cyanthiwigin diterpenes using a cyclopropanation/Cope rearrangement.

Authors:  Laura C Miller; J Maina Ndungu; Richmond Sarpong
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

8.  Desymmetrization of enone-diones via rhodium-catalyzed diastereo- and enantioselective tandem conjugate addition-aldol cyclization.

Authors:  Brian M Bocknack; Long-Cheng Wang; Michael J Krische
Journal:  Proc Natl Acad Sci U S A       Date:  2004-03-15       Impact factor: 11.205

9.  Catalyst control over regio- and enantioselectivity in Baeyer-Villiger oxidations of functionalized ketones.

Authors:  David K Romney; Sean M Colvin; Scott J Miller
Journal:  J Am Chem Soc       Date:  2014-09-29       Impact factor: 15.419

Review 10.  Enantioconvergent catalysis.

Authors:  Justin T Mohr; Jared T Moore; Brian M Stoltz
Journal:  Beilstein J Org Chem       Date:  2016-09-16       Impact factor: 2.883
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