[4 + 2] Cycloadditions
Wiley InterScience Backfile Collection 1832-2000
Chemistry and Pharmacology
Diastereoselective Diels-Alder Reactions with α-Chloronitroso SaccharidesThe α-chloronitroso reagent 2 obtained from ribose via the lactone oxime 3 reacts with the dienes 6-10 at low temperature to give the chiral dihydrooxazines 11-16 in 63-96% yield and 〉 96% enantiomeric excess. The reagents 1 and 2 which are approximately mirror images in the vicinity of the chloronitroso function lead to opposite enantiomers of 11-16. The absolute configuration of the products was determined by chemical degradation and comparison with authentic amino and hydroxy acids.
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