Novel chiral thiazoline-containing N-O ligands in the asymmetric addition of diethylzinc to aldehydes: substituent effect on the enantioselectivity

作者：Gong, Zhiyong; Liu, Qingwen; Xue, Pengchong; Li, Kechang; Song, Zhiguang^*; Liu, Zaiqun; Jin, Yinghua

来源：Applied Organometallic Chemistry, 2012, 26(3): 121-129.

DOI：10.1002/aoc.2820

• thiazoline
• chiral ligands
• imino primary alcohol
• asymmetric addition
• diethylzinc

Several novel chiral thiazoline primary and tertiary alcohols were easily synthesized from commercially available l-cysteine in three steps and with high yield. These ligands were subsequently applied to the asymmetric addition of diethylzinc (Et2Zn) to various aldehydes. Products with S configuration were obtained when thiazoline-containing tertiary alcohol ligands were used as catalysts. The primary alcohol induced corresponding products with R configuration in 68% enantiomeric excess, which was a higher value relative to other N?O ligands possessing a primary alcohol unit in the literature. Furthermore, a plausible transition state model was proposed to explain the observed enantioselectivities.

• 出版日期2012-3
• 单位吉林大学