Prediction of Soai reaction enantioselectivity induced by crystals of N -(2-thienylcarbonyl)glycine

Damien J. Carter, Andrew L. Rohl, Alexander Shtukenberg, Shudan Bian, Chunhua Hu, Lisa Baylon, Bart Kahr, Hiroko Mineki, Koichiro Abe, Tsuneomi Kawasaki, Kenso Soai

Research output: Contribution to journalArticle

Abstract

The enantioselectivity of the autocatalytic alkylation of 2-tert-butylpyrimidyl-5-carbaldehyde, initiated by chiral crystals of N-(2-thienylcarbonyl)glycine, is predicted computationally. The results are in accord with the correlation of the stereochemical outcome of the reaction and the absolute structure of the crystals determined by the anomalous dispersion of X-rays and circular dichroism spectroscopy.

Original languageEnglish (US)
Pages (from-to)2138-2145
Number of pages8
JournalCrystal Growth and Design
Volume12
Issue number4
DOIs
StatePublished - Apr 4 2012

ASJC Scopus subject areas

  • Chemistry(all)
  • Materials Science(all)
  • Condensed Matter Physics

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    Carter, D. J., Rohl, A. L., Shtukenberg, A., Bian, S., Hu, C., Baylon, L., Kahr, B., Mineki, H., Abe, K., Kawasaki, T., & Soai, K. (2012). Prediction of Soai reaction enantioselectivity induced by crystals of N -(2-thienylcarbonyl)glycine. Crystal Growth and Design, 12(4), 2138-2145. https://doi.org/10.1021/cg300207d