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手性催化二有机锌试剂与吡唑-4,5-二酮和吲哚啉-2,3-二酮的不对称加成反应。

Catalytic Asymmetric Addition of Diorganozinc Reagents to Pyrazole-4,5-Diones and Indoline-2,3-Diones.

机构信息

Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu, 610041, P. R. China.

Engineering Center of Catalysis and Synthesis for Chiral Molecules, Department of Chemistry, Fudan University, Shanghai, 200433, P. R. China.

出版信息

Chemistry. 2021 Mar 1;27(13):4302-4306. doi: 10.1002/chem.202005081. Epub 2021 Feb 8.

DOI:10.1002/chem.202005081
PMID:33453077
Abstract

The catalytic enantioselective diorganozinc additions to cyclic diketones including pyrazolin-4,5-diones and isatins have been developed. In the presence of morpholine-containing chiral amino alcohol ligand, the corresponding chiral cyclic tertiary alcohols were produced in good to excellent yields (up to 97 %) and enantioselectivities (up to 95 % ee). The notable feature of this protocol includes its mild reaction conditions, Lewis acid additives free and broad functional group tolerance.

摘要

发展了包括吡唑啉-4,5-二酮和色满酮在内的环状二酮的催化对映选择性二有机锌加成反应。在含有吗啉的手性氨基醇配体存在下,以良好至优秀的收率(高达 97%)和对映选择性(高达 95%ee)得到相应的手性环状叔醇产物。该方法的显著特点包括其温和的反应条件、无路易斯酸添加剂以及对宽官能团的容忍性。

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