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Digitale Medien

Highly Functionalized Bicyclo[3.2.1]octane Derivatives from Readily Available 2′-Alkoxytricyclo[3.2.1.02,7]octanes: Building Blocks for Terpenes, Part I (1998)

de Meijere, Armin ; Hadjiarapoglou, Lazaros ; Noltemeyer, Mathias ; [weitere]

Weinheim : Wiley-Blackwell

Liebigs Annalen 1998 (1998), S. 441-451

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ISSN: 1434-193X

Schlagwort(e): Cascade reaction ; Aprotic Michael reaction ; Tricyclo[3.2.1.02,7]octanes ; Bicyclo[3.2.1]octanes ; Deprotonated cyclopropanes ; Chemistry ; General Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: 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.

Materialart: Digitale Medien

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Digitale Medien

Cascade reactions with chiral michael acceptors; synthesis of enantiomerically pure tricyclo[3.2.1.02,7]- and bicyclo[3.2.1]octanesDedicated to Professor Dr. Wolfgang Lüttke, Georg-August-Universität Göttingen, on the occasion of his 75th birthday. (1995)

Braun, Norbert A. ; Klein, Iris ; Spitzner, Dietrich ; [weitere]

Weinheim : Wiley-Blackwell

Liebigs Annalen 1995 (1995), S. 2165-2169

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ISSN: 0947-3440

Schlagwort(e): Peterson olefination ; Horner Emmons olefination ; Diastereoselective aprotic Michael cascade reaction ; Tricyclo[3.2.1.02,7]octanes ; Bicyclo[3.2.1]octanes ; Chemistry ; Organic Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: Starting from the easily accesible chiral aldehyde 2, we obtained enantiomerically pure (Z)- and (E)-α,-chloro-α,β-unsaturated esters 4c in good yields by olefination reactions. (Z)-and (E)-4c were allowed to react with the kinetically controlled generated lithium dienolate Li-7 to give the enantiomerically pure tricyclo[3.2.1.02,7]octanes 8 and 9, respectively. The „push-pull“ substituted cyclopropane moiety of 8 was opened to give solely bicyclo[3.2.1]octane 10.

Materialart: Digitale Medien

URL: http://dx.doi.org/10.1002/jlac.1995199512302

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