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

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Enantioselectivity
glycine
Glycine
Amino acids
Circular dichroism spectroscopy
Crystals
alkylation
Alkylation
predictions
dichroism
crystals
X rays
spectroscopy
x rays

ASJC Scopus subject areas

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

Cite this

Carter, D. J., Rohl, A. L., Shtukenberg, A., Bian, S., Hu, C., Baylon, L., ... 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

Prediction of Soai reaction enantioselectivity induced by crystals of N -(2-thienylcarbonyl)glycine. / Carter, Damien J.; Rohl, Andrew L.; Shtukenberg, Alexander; Bian, Shudan; Hu, Chunhua; Baylon, Lisa; Kahr, Bart; Mineki, Hiroko; Abe, Koichiro; Kawasaki, Tsuneomi; Soai, Kenso.

In: Crystal Growth and Design, Vol. 12, No. 4, 04.04.2012, p. 2138-2145.

Research output: Contribution to journalArticle

Carter, DJ, Rohl, AL, 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, vol. 12, no. 4, pp. 2138-2145. https://doi.org/10.1021/cg300207d
Carter, Damien J. ; Rohl, Andrew L. ; Shtukenberg, Alexander ; Bian, Shudan ; Hu, Chunhua ; Baylon, Lisa ; Kahr, Bart ; Mineki, Hiroko ; Abe, Koichiro ; Kawasaki, Tsuneomi ; Soai, Kenso. / Prediction of Soai reaction enantioselectivity induced by crystals of N -(2-thienylcarbonyl)glycine. In: Crystal Growth and Design. 2012 ; Vol. 12, No. 4. pp. 2138-2145.
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AU - Kahr, Bart

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