62096-80-4Relevant academic research and scientific papers
Enantioselective Synthesis of 3-Substituted 4-Aroyl-γ-lactones
Roux, Marie-Claude,Patel, Seetal,Merienne, Claude,Morgant, Georges,Wartski, Lya
, p. 809 - 816 (2007/10/03)
Michael addition of the lithiated chiral acyl equivalent 1 to 2-butenolide 2 afforded the (4R)-aroyl-γ-lactone 9 with an enantiomeric excess (ee) value >/= 99percent.Michael addition of 1 to 2 and subsequent alkylation provided (3S)-substituted (4R)-aroyl-γ-lactones 12 and 14 with an ee value of 60 to 65percent and enantiomerically pure lactones 10, 11 and 13.The absolute configuration of the Michael adduct 7 was unequivocally established by X-ray crystal analysis and consequently that of all γ-lactones 9-14 could be deduced. - Keywords: asymmetric Michael addition-protonation; asymmetric Michael addition-α-alkylation; chiral acyl equivalent; functionalized γ-lactones.
