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Synfacts 2015; 11(1): 0071
DOI: 10.1055/s-0034-1379649
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Metallacycle-Mediated Annulation for the Synthesis of Hydroindanes

Contributor(s):
Paul Knochel
,
Diana Haas
Cheng X, Micalizio GC * Dartmouth College, Hanover, USA
An Annulation Reaction for the Synthesis of Cross-Conjugated Triene-Containing Hydroindanes from Acyclic Precursors.

Org. Lett. 2014;
16: 5144-5147
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Further Information

Publication History

Publication Date:
15 December 2014 (online)

 
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Key words

titanium - annulation - hydroindanes

Significance

Cheng and Micalizio report a ste­reoselective annulation reaction to afford cross-conjugated triene-containing hydroindanes that are subsequently trapped by a dienophile in a [4+2]-cycloaddition reaction to obtain highly functionalized carbo- and heterocyclic systems.


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Comment

The tendency of products of type A to undergo Diels–Alder-based dimerization upon standing was harnessed to accomplish this reaction cascade of annulation and intermolecular cycloaddition.


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