Organic Letters
Organic Letters
5 years ago

Synthesis of Spirocyclohexadienones through Radical Cascade Reactions Featuring 3-Fold Carbon–Carbon Bond Formation

Synthesis of Spirocyclohexadienones through Radical Cascade Reactions Featuring 3-Fold Carbon–Carbon Bond Formation
Markus R. Heinrich, Nina Hegmann, Lea Prusko
The radical 5-exo cyclization starting from 2-allyloxyphenyldiazonium ions can be employed for the diastereoselective synthesis of ortho-spirocyclohexadienones through a consecutive addition to alkynes. The spirocyclic systems are formed in a radical [2 + 2 + 1] cycloaddition comprising three carbon–carbon formations, of which the final one is an ipso attack onto the aromatic system at the original position of the diazonium-derived aryl radical.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b00676

DOI: 10.1021/acs.orglett.7b00676

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