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

Yonggui Chi; Timothy J. Peelen; Samuel H. Gellman

doi:10.1021/ol051174u

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

Yonggui Chi, Timothy J. Peelen, Samuel H. Gellman^*

^*Corresponding author for this work

University of Wisconsin-Madison

Research output: Contribution to journal › Article › peer-review

27 Citations (Scopus)

Abstract

(Chemical Equation Presented) In situ derivatization of a variety of α-substituted aldehydes via reaction with chiral amines allows convenient and efficient determination of enantiomeric excess. ¹H 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 α-substituted aldehydes.

Original language	English
Pages (from-to)	3469-3472
Number of pages	4
Journal	Organic Letters
Volume	7
Issue number	16
DOIs	https://doi.org/10.1021/ol051174u
Publication status	Published - Aug 4 2005
Externally published	Yes

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "(Chemical Equation Presented) In situ derivatization of a variety of α-substituted aldehydes via reaction with chiral amines allows convenient and efficient determination of enantiomeric excess. 1H 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 α-substituted aldehydes.",

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N2 - (Chemical Equation Presented) In situ derivatization of a variety of α-substituted aldehydes via reaction with chiral amines allows convenient and efficient determination of enantiomeric excess. 1H 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 α-substituted aldehydes.

AB - (Chemical Equation Presented) In situ derivatization of a variety of α-substituted aldehydes via reaction with chiral amines allows convenient and efficient determination of enantiomeric excess. 1H 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 α-substituted aldehydes.

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

Abstract

ASJC Scopus Subject Areas

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