syn-Diastereoselective glycolate aldol addition reactions of an N(3)-(p-methoxyphenoxy)acetyloxazolidine-2-thione
| Autor: | Craig S. Haynes, Victor L. Leong, Juandah Bruce, Brad J. Austermuehle, Cassie A. Goodman, Shawn R. Hitchcock, Sarah C. Genin, Robert Larson, Christopher G. Hamaker, Austin R. Leise |
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| Rok vydání: | 2017 |
| Předmět: |
1h nmr spectroscopy
010405 organic chemistry Chemistry Stereochemistry Organic Chemistry 010402 general chemistry 01 natural sciences Catalysis 0104 chemical sciences Adduct Inorganic Chemistry chemistry.chemical_compound Aldol reaction Proton NMR Titanium tetrachloride Side chain Physical and Theoretical Chemistry |
| Zdroj: | Tetrahedron: Asymmetry. 28:98-104 |
| ISSN: | 0957-4166 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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