66536-74-1Relevant articles and documents
Enantioselective cross-coupling of meso -epoxides with aryl halides
Zhao, Yang,Weix, Daniel J.
supporting information, p. 3327 - 3340 (2015/03/30)
The first enantioselective cross-electrophile coupling of aryl bromides with meso-epoxides to form trans-β-arylcycloalkanols is presented. The reaction is catalyzed by a combination of (bpy)NiCl2 and a chiral titanocene under reducing conditions. Yields range from 57 to 99% with 78-95% enantiomeric excess. The 30 examples include a variety of functional groups (ether, ester, ketone, nitrile, ketal, trifluoromethyl, sulfonamide, sulfonate ester), both aryl and vinyl halides, and five- to seven-membered rings. The intermediacy of a carbon radical is strongly suggested by the conversion of cyclooctene monoxide to an aryl [3.3.0]bicyclooctanol.
Stereoinversion of arylethanols by Geotrichum candidum
Nakamura, Kaoru,Fujii, Mikio,Ida, Yoshiteru
, p. 3147 - 3153 (2007/10/03)
Aromatic and aliphatic racemic alcohols were converted to the corresponding optically active alcohols in high yield with excellent enantioselectivities by the use of Geotrichum candidum IFO 5767.
Asymmetric reduction of ketones by Geotrichum candidum in the presence of Amberlite Xad, A solid organic solvent
Nakamura, Kaoru,Fujii, Mikio,Ida, Yoshiteru
, p. 3205 - 3211 (2007/10/03)
Asymmetric reduction of ketones by Geotrichum candidum in the presence of Amberlite XAD, a solid organic solvent, was described. A hydrophobic polymer, XAD, was used as material to control the stereochemical course of microbial reductions. Aliphatic and aromatic ketones were reduced to the corresponding (S)-alcohols in excellent enantiomeric excess (ee) in the presence of XRD while low enantioselectivities were observed in the absence of the polymer.