Literature DB >> 16048319

A rapid 1H NMR assay for enantiomeric excess of alpha-substituted aldehydes.

Yonggui Chi1, Timothy J Peelen, Samuel H Gellman.   

Abstract

In situ derivatization of a variety of alpha-substituted aldehydes via reaction with chiral amines allows convenient and efficient determination of enantiomeric excess. (1)H NMR analysis of the imine diastereomer ratio can be conducted immediately after the aldehyde and amine have been mixed. The results correlate well with ee values determined by more traditional (and slower) methods. This approach may be broadly applicable to alpha-substituted aldehydes. [reaction: see text]

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Year:  2005        PMID: 16048319     DOI: 10.1021/ol051174u

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  4 in total

1.  Enantioselective organocatalytic Michael addition of aldehydes to nitroethylene: efficient access to gamma2-amino acids.

Authors:  Yonggui Chi; Li Guo; Nathan A Kopf; Samuel H Gellman
Journal:  J Am Chem Soc       Date:  2008-04-04       Impact factor: 15.419

2.  α-Tetrasubstituted Aldehydes through Electronic and Strain-Controlled Branch-Selective Stereoselective Hydroformylation.

Authors:  Josephine Eshon; Floriana Foarta; Clark R Landis; Jennifer M Schomaker
Journal:  J Org Chem       Date:  2018-08-17       Impact factor: 4.354

3.  A Colorimetric Method for Quantifying Cis and Trans Alkenes Using an Indicator Displacement Assay.

Authors:  Stephanie A Valenzuela; Hannah S N Crory; Chao-Yi Yao; James R Howard; Gabriel Saucedo; A Prasanna de Silva; Eric V Anslyn
Journal:  Angew Chem Int Ed Engl       Date:  2021-05-13       Impact factor: 16.823

4.  Multigramme synthesis and asymmetric dihydroxylation of a 4-fluorobut-2E-enoate.

Authors:  James A B Laurenson; John A Parkinson; Jonathan M Percy; Giuseppe Rinaudo; Ricard Roig
Journal:  Beilstein J Org Chem       Date:  2013-11-26       Impact factor: 2.883

  4 in total

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