ISSN:
0009-2940
Keywords:
Heterobicyclo[3.3.0]octanes, homochiral
;
Amino acids
;
Nitrones
;
Cycloadditions, diastereoselective, intramolecular
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Synthesis of Homochiral 3-Oxa-2,7-diazabicyclo[3.3.0]octanes from Amino Acids by Intramolecular 1,3-Dipolar Cycloaddition of NitronesN1-Allylamino alcohols 9 were prepared from amino acids by various methods. Swern oxidation of 9 afforded aldehydes 11. By reaction of 11 with N1-alkylhydroxylamines nitrone intermediates 4 were formed which spontaneously underwent an intramolecular 1,3-dipolar cycloaddition to yield the bicyclic compounds 6. The cycloaddition proceeds diastereoselectively furnishing homochiral compounds 6 from homochiral starting materials. The structure of 6aA was confirmed by X-ray structural analysis.
Additional Material:
2 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19931260333
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