REGIOSELECTIVITY AND DIASTEREOSELECTIVITY IN THE INDIUM-MEDIATED HOMOALLYL-CYCLOPROPANATION OF DIBENZYLIDENE ACETONE (DBA)

Authors
CAPPS SM LLOYDJONES GC MURRAY M PEAKMAN TM WALSH KE
Citation
Sm. Capps et al., REGIOSELECTIVITY AND DIASTEREOSELECTIVITY IN THE INDIUM-MEDIATED HOMOALLYL-CYCLOPROPANATION OF DIBENZYLIDENE ACETONE (DBA), Tetrahedron letters, 39(18), 1998, pp. 2853-2856
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
18
Year of publication
1998
Pages
2853 - 2856
Database
ISI
SICI code
0040-4039(1998)39:18<2853:RADITI>2.0.ZU;2-J
Abstract
Indium mediated reaction of dibenzylidene acetone (dba) with [H-2(2)]- allyl bromide affords 1,1-distyryl-2-(but-3-enyl) cyclopropane 7 (a tr iene) as a mixture of four isotopomers. Whilst this reaction is not re giospecific, the analogous reaction employing crotyl bromide in place of allyl bromide is highly regioselective and somewhat selective for t he cis cyclopropane isomer. When the reaction is performed with dimeth ylallyl bromide, cyclopropanation fails and tetraene products are obta ined instead. (C) 1998 Elsevier Science Ltd. All rights reserved.