ISSN:
0170-2041
Keywords:
Asymmetric synthesis
;
[4 + 2] Cycloadditions
;
1,2-Oxazines
;
Carbohydrates
;
Saccharides
;
Diels-Alder reactions
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199319930146
