Copper-catalysed asymmetric conjugate addition of organometallic reagents to linear enones using thiourethane ligands

In the presence of chiral thiourethane ligands [Cu(MeCN) 4]BF 4 forms active catalysts for the conjugate addition of MeMgBr, ZnEt 2 and AlR 3 (R = Me, Et) to non-3-en-2-one, hept-3-en-2-one, and 5-methylhex-3-en-2-one. Enantioselectivities of up to 51% are realised for these difficult substrates; fo...

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Bibliographic Details
Published inTetrahedron letters Vol. 40; no. 9; pp. 1767 - 1770
Main Authors Bennett, Simon M.W., Brown, Stephen M., Muxworthy, James P., Woodward, Simon
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 26.02.1999
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ORGANOCOPPER
GRIGNARD-REAGENTS
1,4-ADDITION
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Summary:In the presence of chiral thiourethane ligands [Cu(MeCN) 4]BF 4 forms active catalysts for the conjugate addition of MeMgBr, ZnEt 2 and AlR 3 (R = Me, Et) to non-3-en-2-one, hept-3-en-2-one, and 5-methylhex-3-en-2-one. Enantioselectivities of up to 51% are realised for these difficult substrates; for cyclohex-2-enone an e.e. of 42% is attained. Thiourethane ligands, previously untried in asymmetric catalysis, are effective in the copper(I) promoted additions to challenging linear enones.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(98)02686-0