Long-range shielding effects in the 1H NMR spectra of mosher-like ester derivatives

Thomas R. Hoye, Sara E. Erickson, Sherrie L. Erickson-Birkedahl, Christopher R.H. Hale, Enver Cagri Izgu, Michael J. Mayer, Patrick K. Notz, Matthew K. Renner

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

Abstract

The relative magnitudes of the chemical shift differences (δσs) in the two diastereomers of menthyl esters of known chiral derivatizing agents (CDAs) were compared to those of the α-methoxy-α-trifluoromethyl-1- naphthylacetyl (MTN(1)A) analogues I. Discrimination of the terminal diastereotopic methyl resonances in esters of the homologous, symmetrical carbinols II was evaluated. Remarkably, the methyls differed in the MTN (1)A esters III even when n = 15; an unexpected crossover in the sign of the δσ values was also observed.

Original languageEnglish (US)
Pages (from-to)1768-1771
Number of pages4
JournalOrganic Letters
Volume12
Issue number8
DOIs
StatePublished - Apr 16 2010

Fingerprint

Dive into the research topics of 'Long-range shielding effects in the 1H NMR spectra of mosher-like ester derivatives'. Together they form a unique fingerprint.

Cite this