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

• Published in: Tetrahedron 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
• Language: English
• Published: OXFORD Elsevier Ltd 26.02.1999; Elsevier
• Subjects: Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology; ORGANOCOPPER; GRIGNARD-REAGENTS; 1,4-ADDITION

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...