State Key Laboratory of Fine Chemicals, School of Pharmaceutical Science and Technology, Dalian University of Technology, Dalian 116024, China.
J Org Chem. 2012 Nov 2;77(21):9601-8. doi: 10.1021/jo3016242. Epub 2012 Oct 18.
Cinchona alkaloid-derived chiral quaternary ammonium organocatalysts were developed. The catalyst with a bulky 1-adamantoyl group at the C-9 position promoted the enantioselective α-hydroxylation of β-oxo esters and resulted in the corresponding products in 35-95% yields and 58-90% ee. The reaction was successfully scaled to a gram-quantity scale with a similar yield without loss of enantioselectivity.
开发了金鸡纳生物碱衍生的手性季铵盐有机催化剂。在 C-9 位具有大体积 1-金刚烷酰基的催化剂促进了β-氧代酯的对映选择性α-羟化反应，得到了相应的产物，产率为 35-95%，ee 值为 58-90%。反应可以成功地放大到克级规模，产率相似，对映选择性没有损失。
