90865-33-1Relevant academic research and scientific papers
Preparation of chiral 3-oxocycloalkanecarbonitrile and its derivatives by crystallization-induced diastereomer transformation of ketals with chiral 1,2-diphenylethane-1,2-diol
Yamashita, Yohei,Maki, Daisuke,Sakurai, Shiho,Fuse, Takumi,Matsumoto, Shoji,Akazome, Motohiro
, p. 32601 - 32609 (2018/10/15)
Chiral 3-oxocycloalkanecarbonitriles were prepared by fractional crystallization and crystallization-induced diastereomer transformation (CIDT) of diastereomeric ketals with (1R,2R)-1,2-diphenylethane-1,2-diol. Investigation of the crystal structures by X
Identification and Implementation of Biocatalytic Transformations in Route Discovery: Synthesis of Chiral 1,3-Substituted Cyclohexanone Building Blocks
Hadi, Timin,D?az-Rodr?guez, Alba,Khan, Diluar,Morrison, James P.,Kaplan, Justin M.,Gallagher, Kathleen T.,Schober, Markus,Webb, Michael R.,Brown, Kristin K.,Fuerst, Douglas,Snajdrova, Radka,Roiban, Gheorghe-Doru
supporting information, p. 871 - 879 (2018/07/05)
Several biocatalytic approaches for the preparation of optically pure methyl 3-oxocyclohexanecarboxylates (S)-, (R)-1 and 3-oxocyclohexanecarbonitriles (S)-, (R)-2 have been successfully demonstrated. Screening of reaction-focused enzyme collections was used to identify initial hits using three enzymatic strategies. Reaction optimization and scale-up enabled the production of chiral intermediates for route scouting efforts on scales of up to 100 g. The enzymes applied in these processes (lipases, enoate reductases, and nitrilases) have been shown to be robust catalysts for drug manufacturing and represent a green alternative to conventional methods to access these chiral cyclohexanone building blocks.
A catalytic enantioselective conjugate addition of cyanide to enones
Tanaka, Yuta,Kanai, Motomu,Shibasaki, Masakatsu
, p. 6072 - 6073 (2008/12/20)
The first synthetically useful catalytic enantioselective conjugate addition of cyanide to enones is described. The optimized conditions involved a Gd catalyst (5 or 10 mol %) derived from ligands 3 or 4 and a 1:1 ratio of TBSCN and 2,6-dimethylphenol. Th
ENZYMATIC IN VITRO REDUCTION OF KETONES. PART 11. THE UNEXPECTED STERIC COURSE OF THE HLAD CATALYZED REDUCTION OF 3-CYANOCYCLOHEXANONE.
Willaert, Jan J.,Lemiere, Guy L.,Dommisse, Roger A.,Lepoivre, Joseph A.,Alderweireldt, Frank C.
, p. 139 - 150 (2007/10/02)
3-Cyanocyclohexanone is a suitable substrate for preparative HLAD reduction, delivering enantiomerically pure (1S,3S)-trans and (1R,3S)-cis alcohols.Details are given on the kinetics of the reduction and the absolute configuration of the products.In contr
