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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.


Proposed use of 2-bromo(hetero)aryl aldehydes in Cannizzaro-triggered annulation cascades compared to traditional approaches. EWG=electron-withdrawing group, LA=Lewis acid, R1–R3 are generic groups, n and m are typically 0–1.
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sch1: Proposed use of 2-bromo(hetero)aryl aldehydes in Cannizzaro-triggered annulation cascades compared to traditional approaches. EWG=electron-withdrawing group, LA=Lewis acid, R1–R3 are generic groups, n and m are typically 0–1.


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)

Proposed use of 2-bromo(hetero)aryl aldehydes in Cannizzaro-triggered annulation cascades compared to traditional approaches. EWG=electron-withdrawing group, LA=Lewis acid, R1–R3 are generic groups, n and m are typically 0–1.
© Copyright Policy
Related In: Results  -  Collection

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getmorefigures.php?uid=PMC4581465&req=5

sch1: Proposed use of 2-bromo(hetero)aryl aldehydes in Cannizzaro-triggered annulation cascades compared to traditional approaches. EWG=electron-withdrawing group, LA=Lewis acid, R1–R3 are generic groups, n and m are typically 0–1.
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.