109053-85-2Relevant academic research and scientific papers
An Insoluble Copper(II) Acetylacetonate-Chiral Bipyridine Complex that Catalyzes Asymmetric Silyl Conjugate Addition in Water
Kitanosono, Taku,Zhu, Lei,Liu, Chang,Xu, Pengyu,Kobayashi, Shu
supporting information, p. 15422 - 15425 (2015/12/26)
Acicular purplish crystals were obtained from Cu(acac)2 and a chiral bipyridine ligand. Although the crystals were not soluble, they nevertheless catalyzed asymmetric silyl conjugate addition of lipophilic substrates in water. Indeed, the reactions proceeded efficiently only in water; they did not proceed well either in organic solvents or in mixed water/organic solvents in which the catalyst/substrates were soluble. This is in pronounced contrast to conventional organic reactions wherein the catalyst/substrates tend to be in solution. Several advantages of the chiral Cu(II) catalysis in water over previously reported catalyst systems have been demonstrated. Water is expected to play a prominent role in constructing and stabilizing sterically confined transition states and accelerating subsequent protonation to achieve high yields and enantioselectivities.
Preparation of Enantiomerically Pure β-Silylcarboxyl Derivatives by Asymmetric 1,4-Addition to N-Enoyl-sultams
Oppolzer, Wolfgang,Mills, Robert J.,Pachinger, Werner,Stevenson, Thomas
, p. 1542 - 1545 (2007/10/02)
EtAlCl2-promoted additions of organocopper reagents to camphor-derived, conjugated N-enoyl-sultams gave saturated and olefinic β-silylcarboxyl derivatives with high diastereodifferentiation.Nondestructive removal of the chiral auxiliary followed by oxidative Si-C bond cleavage furnished enantiomerically pure acetate-derived aldols and propionate-derived 'anti'-aldols (via silyl-directed α-methylation).
