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Regioselectivity and diastereoselectivity in the indium-mediated homoallyl-cyclopropanation of dibenzylidene acetone (dba)

โœ Scribed by Steven M. Capps; Guy C. Lloyd-Jones; Martin Murray; Torren M. Peakman; Kenneth E. Walsh

Book ID
104259043
Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
247 KB
Volume
39
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Indium mediated reaction of dibenzylidene acetone (dba) with [2H2]-allyl bromide affords 1,l-distyryl-2-(but-3-enyl) cyclopropane 7 (a triene) as a mixture of four isotopomers. Whilst this reaction is not regiospecific, the analogous reaction employing crotyl bromide in place of allyl bromide is highly regioselective and somewhat selective for the cis cyclopropane isomer. When the reaction is performed with dimethylallyl bromide, cyclopropanation fails and tetraene products are obtained instead.

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