Limits...
One-Pot Cannizzaro Cascade Synthesis of ortho-Fused Cycloocta-2,5-dien-1-ones from 2-Bromo(hetero)aryl Aldehydes.

Burroughs L, Eccleshare L, Ritchie J, Kulkarni O, Lygo B, Woodward S, Lewis W - Angew. Chem. Int. Ed. Engl. (2015)

Bottom Line: An intramolecular Cannizzaro-type hydride transfer to an in situ prepared allene enables the synthesis of ortho-fused 4-substituted cycloocta-2,5-dien-1-ones with unprecedented technical ease for an eight-ring carboannulation.Various derivatives could be obtained from commercially available (hetero)aryl aldehydes, trimethylsilylacetylene, and simple propargyl chlorides in good yields.

View Article: PubMed Central - PubMed

Affiliation: School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD (UK).

No MeSH data available.


Mechanistic proposal for the formation of eight-ring compounds 4; L is indicative of the presence of a generic organocopper or -cuprate species.
© Copyright Policy
Related In: Results  -  Collection


getmorefigures.php?uid=PMC4581465&req=5

sch4: Mechanistic proposal for the formation of eight-ring compounds 4; L is indicative of the presence of a generic organocopper or -cuprate species.


One-Pot Cannizzaro Cascade Synthesis of ortho-Fused Cycloocta-2,5-dien-1-ones from 2-Bromo(hetero)aryl Aldehydes.

Burroughs L, Eccleshare L, Ritchie J, Kulkarni O, Lygo B, Woodward S, Lewis W - Angew. Chem. Int. Ed. Engl. (2015)

Mechanistic proposal for the formation of eight-ring compounds 4; L is indicative of the presence of a generic organocopper or -cuprate species.
© Copyright Policy
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC4581465&req=5

sch4: Mechanistic proposal for the formation of eight-ring compounds 4; L is indicative of the presence of a generic organocopper or -cuprate species.
Bottom Line: An intramolecular Cannizzaro-type hydride transfer to an in situ prepared allene enables the synthesis of ortho-fused 4-substituted cycloocta-2,5-dien-1-ones with unprecedented technical ease for an eight-ring carboannulation.Various derivatives could be obtained from commercially available (hetero)aryl aldehydes, trimethylsilylacetylene, and simple propargyl chlorides in good yields.

View Article: PubMed Central - PubMed

Affiliation: School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD (UK).

No MeSH data available.