Cover Picture: Using a Tripod as a Chiral Chelating Ligand: Chemical Exchange Between Equivalent Molecular Structures in Palladium Catalysis with 1,1,1‐Tris(oxazolinyl)ethane (“Trisox”) (Chem. Eur. J. 21/2007)
“…The same behavior was observed with the 2-bromo-4-substituted oxazolines 1a − c . Among all substrates studied, the (4R,5S)-2-bromo-4,5-indanediyloxazoline ( 1d ) was found to be the least stable derivative, and suitable crystals of the product 2d for an X-ray diffraction study were obtained (Scheme and Figure ), thus establishing the details of the molecular structure of the compound 2 Diastereoselective Conversion of the (4 R ,5 S )-2-Bromo-4,5-indandiyloxazoline 1d into 2-Bromo-1-isocyanato-2,3-dihydro-1 H -indene 2d (Neat, 25 °C, 5 min) 2 Molecular structure of (1 R ,2 R )-2-bromo-1-isocyanato-2,3-dihydro-1 H -indene 2d .…”
A unprecedented thermally induced rearrangement of 2-bromo-4-substituted oxazolines into 2-bromoisocyanates with high selectivity has been observed. Isolated yields of 85-90% were obtained with 2-bromo-4-phenyloxazoline, 2-bromo-4-isopropyloxazoline, or 2-bromo-4,4-dimethyloxazoline. In addition, chiral aziridinecarboxamides or 2-aminooxazolines could be selectively obtained from the corresponding 2-bromo isocyanate depending on reaction conditions.
“…The same behavior was observed with the 2-bromo-4-substituted oxazolines 1a − c . Among all substrates studied, the (4R,5S)-2-bromo-4,5-indanediyloxazoline ( 1d ) was found to be the least stable derivative, and suitable crystals of the product 2d for an X-ray diffraction study were obtained (Scheme and Figure ), thus establishing the details of the molecular structure of the compound 2 Diastereoselective Conversion of the (4 R ,5 S )-2-Bromo-4,5-indandiyloxazoline 1d into 2-Bromo-1-isocyanato-2,3-dihydro-1 H -indene 2d (Neat, 25 °C, 5 min) 2 Molecular structure of (1 R ,2 R )-2-bromo-1-isocyanato-2,3-dihydro-1 H -indene 2d .…”
A unprecedented thermally induced rearrangement of 2-bromo-4-substituted oxazolines into 2-bromoisocyanates with high selectivity has been observed. Isolated yields of 85-90% were obtained with 2-bromo-4-phenyloxazoline, 2-bromo-4-isopropyloxazoline, or 2-bromo-4,4-dimethyloxazoline. In addition, chiral aziridinecarboxamides or 2-aminooxazolines could be selectively obtained from the corresponding 2-bromo isocyanate depending on reaction conditions.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.
