Synthesis of quinazolinone-based aziridine diols as chiral ligands: dual stereoselectivity in the asymmetric ethylation of aryl aldehydes
Özet
A new class of quinazoline-based enantiomerically pure aziridine diols 4a-d were prepared from the aziridination of mesityl oxide 3 with in situ generated 3-acetoxyaminoquinazolinone (S)-2b followed by NaBH4 reduction. Aziridine diols 4a-d were purified by means of column chromatography on silica gel and their stereochemistries were assigned by X-ray crystallography and NMR analysis. These aziridine diols 4 were evaluated as chiral ligands in the asymmetric addition of diethylzinc to aryl aldehydes, and ligand (S,R,R)-4a yielded (R)-1-phenylpropanol derivatives with up to 92% ee, while the diastereomer (S,S,R)-4c gave the opposite enantiomers (S)-1-phenylpropanol derivatives with up to 86% ee. The results demonstrate that switching the configuration of the aziridine alcohol moiety in ligand gives a remarkable reversal of enantioselectivity in the asymmetric addition of diethylzinc to aryl aldehydes. (C) 2015 Elsevier Ltd. All rights reserved.
Atıf için künye
CELIK, S., Çakıcı, M., Kılıç, H., & Şahin, E. (2015). Synthesis of quinazolinone-based aziridine diols as chiral ligands: dual stereoselectivity in the asymmetric ethylation of aryl aldehydes. TETRAHEDRON-ASYMMETRY, 26, 152–157. https://doi.org/10.1016/j.tetasy.2014.12.011
BibTeX
@article{celik2015-66685,
author = {CELIK, Saffet and Çakıcı, Murat and Kılıç, Hamdullah and Şahin, Ertan},
title = {Synthesis of quinazolinone-based aziridine diols as chiral ligands: dual stereoselectivity in the asymmetric ethylation of aryl aldehydes},
journal = {TETRAHEDRON-ASYMMETRY},
year = {2015},
volume = {26},
pages = {152--157},
issn = {0957-4166},
doi = {10.1016/j.tetasy.2014.12.011},
url = {https://akademik.atauni.edu.tr/yayinlar/66685-synthesis-of-quinazolinone-based-aziridine-diols-as-chiral-ligands-dual}
}