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Highly Enantioselective Conjugate Addition of AlMe 3 to Linear Aliphatic Enones by a Designed Catalyst
Author(s) -
Fraser Paul K.,
Woodward Simon
Publication year - 2003
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200390087
Subject(s) - conjugate , enantioselective synthesis , catalysis , chemistry , hydrolysis , ligand (biochemistry) , addition reaction , medicinal chemistry , organic chemistry , stereochemistry , mathematics , receptor , mathematical analysis , biochemistry
2‐Hydroxy‐2′‐alkylthio‐1,1′‐binaphthyl compounds are catalytic promoters of the 1,4‐addition of AlMe 3 to linear aliphatic enones in THF at −40 to −48 °C in the presence of [Cu(MeCN) 4 ]BF 4 . At ligand loadings of 5–20 mol %, enantioselectivities of 80–93 % are realised for most substrates. To attain these values, the use of highly pure AlMe 3 is mandatory. The presence of methylalumoxane (MAO), derived by hydrolysis, leads to reduced enantioselectivity and a conjugate addition product.