The reaction of nitrile oxides 2 or nitrones 5 with chiral and optically pure methyl enol ethers of (R(s))-1-fluoroalkyl-2-(p-tolylsulfinyl)ethanones 1 leads with high regio-and diastereo-selectivity to the (4S,5R,R(S))-4,5-dihydroisoxazoles 3 or (3S,4S,5R,R(S))-isoxazolidines 6; the absolute stereochemistry of the compounds has been determined using X-ray diffraction and NMR analyses.
Asymmetric 1.3-Dipolar cycloadditions of nitrile oxides and nitrones with fluorosubstituted chiral vinyl sulfoxides
CRUCIANELLI, MARCELLO;
1996-01-01
Abstract
The reaction of nitrile oxides 2 or nitrones 5 with chiral and optically pure methyl enol ethers of (R(s))-1-fluoroalkyl-2-(p-tolylsulfinyl)ethanones 1 leads with high regio-and diastereo-selectivity to the (4S,5R,R(S))-4,5-dihydroisoxazoles 3 or (3S,4S,5R,R(S))-isoxazolidines 6; the absolute stereochemistry of the compounds has been determined using X-ray diffraction and NMR analyses.File in questo prodotto:
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