Institute of Microbial Chemistry (BIKAKEN) 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021, Japan.
J Org Chem. 2017 Aug 4;82(15):8304-8308. doi: 10.1021/acs.joc.7b01381. Epub 2017 Jul 19.
Direct asymmetric aldol addition of an α-CF amide to arylglyoxal hydrates was promoted by a chiral catalyst comprising a soft Lewis acidic Cu(I), a chiral bisphosphine ligand, and DBU. The 7-azaindoline moiety of the amide facilitates its enolization and stabilizes the thus-generated Cu enolate, furnishing enantioenriched aldol adducts.
手性铜(I)配合物、双膦配体和 DBU 促进的 α-CF 酰胺与芳基乙二醛水合物的直接不对称羟醛加成。酰胺的 7-氮茚基部分促进其烯醇化并稳定由此产生的 Cu 烯醇化物,提供对映体富集的羟醛加成产物。