Enantioselective Recognition of Amino Alcohols and Amino Acids by Chiral Binol- Based Aldehydes with Conjugated Rings at the Hydrogen Bonding Donor Sites

Bulletin of the Korean chemical society

Kwan Mook Kim¹  Jiyoung Kim¹  Raju Nandhakumar¹ 

关键词: Chiral aldehyde;    Chirality conversion;    Enantioselective imine formation;    Amino alcohols;    Amino acids;   

DOI  :  

学科分类：化学（综合）

来源: Korean Chemical Society

【 摘 要 】

Novel binol-based uryl and guanidinium receptors having higher ring conjugation at the periphery of the hydrogen bonding donor sites have been synthesized and utilized to study the enantioselective recognition of 1,2-aminoalcohols and chirality conversion of natural amino acids via imine bond formation. There is a remarkable decrease in the stereoselectivites as the conjugation increases at the periphery of hydrogen bonding donor sites. The guanidinium-based receptors show more selectivity towards the amino alcohol than that of the uryl based ones due to its charge reinforced hydrogen bonds. The conversion efficiency of L-amino acids to Damino acids by the uryl-based receptors is higher than that of the guanidinium-based ones.

【 授权许可】

Unknown