197069-17-3Relevant academic research and scientific papers
Catalytic enantioselective Hosomi-Sakurai reaction of α-ketoesters promoted by chiral copper(ii) complexes
Niwa, Yutaro,Miyake, Mayu,Hayakawa, Ichiro,Sakakura, Akira
, p. 3923 - 3926 (2019)
A catalytic enantioselective Hosomi-Sakurai reaction of α-ketoesters has been developed. A copper(ii) complex with a chiral bis(oxazoline) ligand bearing methanesulfonamide groups shows excellent catalytic activity to give α,α-disubstituted α-hydroxyesters in high yields with high enantioselectivities. This is the first successful method for the catalytic enantioselective 1,2-addition of α-ketoesters with allylic silanes.
Catalytic use of zinc amide for transmetalation with allylboronates: General and efficient catalytic allylation of carbonyl compounds, imines, and hydrazones
Cui, Yi,Li, Wei,Sato, Takehiro,Yamashita, Yasuhiro,Kobayashi, Shu
supporting information, p. 1193 - 1205 (2013/06/04)
The efficient catalytic allylation of ketones, imines, and hydrazones with allylboronates using a catalytic amount of zinc amide is reported. In this reaction, the boron-to-zinc exchange process occurred smoothly to afford the corresponding allylzinc amides, and the desired allylation reactions proceeded in high efficiency (～0.1mol%). A mechanistic study revealed that transmetalation was a rate-determining step in the catalytic cycle, and also that the amide ligand on the zinc center played a key role in preparing reactive allylzinc species. Catalytic asymmetric allylations were also investigated, and high enantioselectivities were obtained using chiral diamine ligands. Copyright
Total synthesis of (-)- and (±)-frontalin via ring-closing metathesis
Scholl, Matthias,Grubbs, Robert H.
, p. 1425 - 1428 (2007/10/03)
Racemic and enantiopure targets containing the 6,8-dioxabicyclo [3.2.1]octane skeleton, can be conveniently synthesized from monocyclic diene precursors using an intramolecular ruthenium-catalyzed ring-closing metathesis reaction as the key step.
Asymmetric Allylation of Carbonyl Compounds with Tartrate-Modified Chiral Allylic Tin Reagents
Yamada, Koji,Tozawa, Takashi,Nishida, Minoru,Mukaiyama, Teruaki
, p. 2301 - 2308 (2007/10/03)
Chiral allylating reagents, readily generated in situ from tin(II) catecholate [SnII(O2C6H4)], allyl halides, chiral dialkyl tartrates, and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), reacted smoothly with aldehydes or reactive ketones at - 78 °C in the presence of a catalytic amount of copper salts to afford the corresponding optically active homoallyl alcohols. Allylation of aromatic aldehydes and pyruvates by the present chiral tin reagents proceeded in high yields (81-99%) with high enantioselectivities (89-94%ee). In addition, both enantiomers of dimethyl citramalate were prepared from the allylation products of benzyl pyruvate.
