Ring Opening and Rearrangement Reactions of Tricyclo[4.2.1.02,5]nonan-9-one

Ingbert Braun; Florian Rudroff; Marko D. Mihovilovic; Thorsten Bach

doi:10.1055/s-2007-990937

PAPER

Ring Opening and Rearrangement Reactions of Tricyclo[4.2.1.0^2,5]nonan-9-one

Ingbert Braun^a, Florian Rudroff^b, Marko D. Mihovilovic^b, Thorsten Bach*^a
^a Lehrstuhl für Organische Chemie I, Technische Universität München, Lichtenbergstr. 4, 85747 Garching, Germany
Fax: +49(89)28913315; e-Mail: thorsten.bach@ch.tum.de;
^b Institut für Angewandte Synthesechemie, Technische Universität Wien, Getreidemarkt 9/163-OC, 1060 Vienna, Austria

Abstract

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Abstract

A general concept is introduced to synthesize bicyclo[4.2.0]octanes by a sequence of intramolecular copper(I)-catalyzed [2+2] photocycloaddition and subsequent fragmentation reactions. The concept was tested by subjecting the photochemically accessible tricyclo[4.2.1.0^2,5]nonan-9-one to four different ring-opening or rearrangement reactions, which allowed for the formation of functionalized bicyclo[4.2.0]octanes by cleavage of the carbonyl bridge. All four methods investigated, Haller-Bauer cleavage, the Schmidt reaction, Baeyer-Villiger oxidation, and rhodium(II)-catalyzed rearrangement were applicable to tricyclo[4.2.1.0^2,5]nonan-9-one, but they differed with regard to enantioselectivity. Enzymatic Baeyer-Villiger oxidation was the most successful of these methods, also more successful than metal-catalyzed Baeyer-Villiger oxidation, providing access to enantiomerically enriched lactones, for example in 72% yield and 95% ee. The second-most successful method was with a commercially available rhodium catalyst, which effected ring enlargement of tricyclo[4.2.1.0^2,5]nonan-9-one to its homologue in good overall yield and modest enantioselectivity (up to 24% ee).

Key words

cycloadditions - ketones - lactones - photochemistry - ring opening - stereoselective synthesis

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