ISSN:
0947-3440
Keywords:
Dienes, chiral
;
1,3-Dioxin-4-ones
;
(-)-Menthone
;
Diels-Alder reactions, diastereoselective
;
Cycloadditions, high-pressure
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Synthesis and diastereoselective Diels-Alder reactions of new spirocyclic chiral dienes are reported. Starting with diketene and (-)-menthone (1), we prepared the diastereomeric diketene-menthone adducts 2 and 3. Further derivatization and olefination afforded four chiral dienes 12-15. Diastereoselective Diels-Alder reactions of these dienes with N-phenylmaleimide (NPM) under high-pressure conditions yielded the corresponding cycloadducts 16-19. Olefination of 6-diethylphosphonomethyl-2,2-dimethyl-1,3-dioxin-4-one 8 with formaldehyde led to unexpected compounds 9-11 resulting from the originally formed olefination product.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.1995199508198
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