ISSN:
1434-193X
Keywords:
Cascade reaction
;
Aprotic Michael reaction
;
Tricyclo[3.2.1.02,7]octanes
;
Bicyclo[3.2.1]octanes
;
Deprotonated cyclopropanes
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
2′-Alkoxytricyclo[3.2.1.02,7]octanes 4-R are obtained in good to excellent yields from methyl 2-chloro-2-cyclopropylideneacetate (3) and the dienolates derived from the 3-alkoxycyclohex-2-enones 1-R and 2-R, by a cascade of two consecutive Michael additions and a γ-elimination. Compounds 4-R are transformed to the correspondingly substituted bicyclo[3.2.1]octanecarboxylates 5 by treatment with acid. 2′-Methoxytricyclooctanes 4a-d-Me are readily deprotonated to give chelation-stabilized cyclopropyllithium derivatives 6-Me, which react with electrophiles to yield the 7′-substituted tricyclo[3.2.1.02,7]octanes 4f-i-Me (61-66%). By acidic workup of such reaction mixtures, or subsequent treatment of the isolated products 4f-i-Me with acid, efficient transformation to the correspondingly substituted bicyclo[3.2.1]octanecarboxylates 5 is observed.
Type of Medium:
Electronic Resource
