syn-Diastereoselective glycolate aldol addition reactions of an N(3)-(p-methoxyphenoxy)acetyloxazolidine-2-thione |
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Authors: | Craig S Haynes Cassie A Goodman Juandah Bruce Sarah C Genin Brad J Austermuehle Victor L Leong Austin R Leise Robert Larson Christopher G Hamaker Shawn R Hitchcock |
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Institution: | Department of Chemistry, Illinois State University, Normal, IL 61790-4160, USA |
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Abstract: | An N3-(p-methoxyphenoxy)acetyloxazolidine-2-thione has been synthesized and employed in glycolate asymmetric aldol addition reactions with aromatic and aliphatic aldehydes. It was determined that the titanium tetrachloride medicated aldol reaction afforded diastereoselectivities that ranged from 75:25 to 94:6 when the reaction was conducted at ?78 °C. The absolute stereochemistry of the aldol adducts was determined by 1H NMR spectroscopy and X-ray crystallography. The 1H NMR spectra of the aldol adducts contained a signal (the α-proton of the glycolate position of the aldol side chain) that was highly deshielded due to conformational restriction about the N(3)-(p-methoxyphenoxy)acetyl side chain and the oxazolidine-2-thione auxiliary. |
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Keywords: | Corresponding author Tel : 309 438 7854 fax: 309 438 5538 |
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