Literature DB >> 23593963

Determination of absolute configuration of secondary alcohols using thin-layer chromatography.

Alexander J Wagner1, Scott D Rychnovsky.   

Abstract

A new implementation of the competing enantioselective conversion (CEC) method was developed to qualitatively determine the absolute configuration of enantioenriched secondary alcohols using thin-layer chromatography. The entire process for the method requires approximately 60 min and utilizes micromole quantities of the secondary alcohol being tested. A number of synthetically relevant secondary alcohols are presented. Additionally, (1)H NMR spectroscopy was conducted on all samples to provide evidence of reaction conversion that supports the qualitative method presented herein.

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Year:  2013        PMID： 23593963      PMCID： PMC3702370          DOI： 10.1021/jo400432q

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  27 in total

1.  Absolute configuration determination of chiral molecules in the solution state using vibrational circular dichroism.

Authors:  Teresa B Freedman; Xiaolin Cao; Rina K Dukor; Laurence A Nafie
Journal:  Chirality       Date:  2003-11       Impact factor: 2.437

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Authors:  Thomas J Wenzel; Cora D Chisholm
Journal:  Chirality       Date:  2010-09-17       Impact factor: 2.437

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5.  The use of X-ray crystallography to determine absolute configuration.

Authors:  H D Flack; G Bernardinelli
Journal:  Chirality       Date:  2008-05-15       Impact factor: 2.437

6.  Effects of Methyl Substituents on the Activity and Enantioselectivity of Homobenzotetramisole-Based Catalysts in the Kinetic Resolution of Alcohols.

Authors:  Yuhua Zhang; Vladimir B Birman
Journal:  Adv Synth Catal       Date:  2009-10-01       Impact factor: 5.837

7.  13C NMR as a general tool for the assignment of absolute configuration.

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Journal:  Chem Commun (Camb)       Date:  2010-10-01       Impact factor: 6.222

8.  Determination of absolute configuration using kinetic resolution catalysts.

Authors:  Alexander J Wagner; Jonathan G David; Scott D Rychnovsky
Journal:  Org Lett       Date:  2011-07-21       Impact factor: 6.005

Review 9.  Determination of absolute configuration of secondary alcohols using lipase-catalyzed kinetic resolutions.

Authors:  Qing Jing; Romas J Kazlauskas
Journal:  Chirality       Date:  2008-05-15       Impact factor: 2.437

10.  Homobenzotetramisole: an effective catalyst for kinetic resolution of aryl-cycloalkanols.

Authors:  Vladimir B Birman; Ximin Li
Journal:  Org Lett       Date:  2008-02-16       Impact factor: 6.005
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  3 in total

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Authors:  Ivelina M Yonova; A George Johnson; Charlotte A Osborne; Curtis E Moore; Naomi S Morrissette; Elizabeth R Jarvo
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3.  Functional-group-tolerant, nickel-catalyzed cross-coupling reaction for enantioselective construction of tertiary methyl-bearing stereocenters.

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Journal:  J Am Chem Soc       Date:  2013-06-10       Impact factor: 15.419
  3 in total

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