Synthesis of quinazolinone-based aziridine diols as chiral ligands: dual stereoselectivity in the asymmetric ethylation of aryl aldehydes
作者： Saffet Celik , Murat Cakici , Hamdullah Kilic , Ertan Sahin
DOI: 10.1016/J.TETASY.2014.12.011
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摘要: Abstract A new class of quinazoline-based enantiomerically pure aziridine diols 4a–d were prepared from the aziridination mesityl oxide 3 with in situ generated 3-acetoxyaminoquinazolinone (S)-2b followed by NaBH4 reduction. Aziridine purified means column chromatography on silica gel and their stereochemistries assigned X-ray crystallography NMR analysis. These 4 evaluated as chiral ligands asymmetric addition diethylzinc to aryl aldehydes, ligand (S,R,R)-4a yielded (R)-1-phenylpropanol derivatives up 92% ee, while diastereomer (S,S,R)-4c gave opposite enantiomers (S)-1-phenylpropanol 86% ee. The results demonstrate that switching configuration alcohol moiety gives a remarkable reversal enantioselectivity aldehydes.
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