Reiners, I.; Wilken, J.; Martens, J. published their research in Tetrahedron: Asymmetry on December 31 ,1995. The article was titled 《Intramolecular vs. intermolecular induction in the diastereoselective catalytic reduction of enantiomerically pure ketones with borane in the presence of cyclic β-amino alcohols》.Electric Literature of C10H14ClNO2 The article contains the following contents:
Asym. reduction of various enantiomerically pure ketones was carried out by using oxazaborolidine catalysts with a variety of achiral and chiral ligands. The efficiency of chiral 1,2-amino alcs. as well as the effect of the stereogenic centers in the substrate on the catalytic asym. reduction were studied. The products obtained from (2S-trans)-5-methyl-2-(1-methylethyl)cyclohexanone (menthone) were (1R-endo)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol [(+)-borneol] and (1R-exo)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol [(-)-isoborneol]. The products from (1R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one [(+)-camphor] were [1R-1α,2β,5α]-5-methyl-2-(1-methylethyl)cyclohexanol [(+)-neoisomenthol] and [(+)-neoisomenthol]. It was found that the corresponding secondary alcs. were obtained with extremely high stereoselectivities with the proper choice of chiral ligands although a considerably large double asym. induction was observed in some cases. The experimental process involved the reaction of H-Phg-OEt.HCl(cas: 59410-82-1Electric Literature of C10H14ClNO2)
H-Phg-OEt.HCl(cas: 59410-82-1) belongs to esters. Esters are more polar than ethers but less polar than alcohols. Electric Literature of C10H14ClNO2 They participate in hydrogen bonds as hydrogen-bond acceptors, but cannot act as hydrogen-bond donors, unlike their parent alcohols. This ability to participate in hydrogen bonding confers some water-solubility.
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics