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

Rong-Hui Wang; Ya-Ling Li; Hong-Jiao He; You-Cai Xiao; Fen-Er Chen

doi:10.1002/chem.202005081

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

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

Authors

Rong-Hui Wang¹, Ya-Ling Li¹, Hong-Jiao He¹, You-Cai Xiao¹, Fen-Er Chen^{1

2

3}

Affiliations

¹ Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu, 610041, P. R. China.
² Engineering Center of Catalysis and Synthesis for Chiral Molecules, Department of Chemistry, Fudan University, Shanghai, 200433, P. R. China.
³ Shanghai Engineering Center of, Industrial Asymmetric Catalysis for Chiral Drugs, Shanghai, 200433, P. R. China.

PMID: 33453077
DOI: 10.1002/chem.202005081

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.

Keywords: chiral amino alcohol; diorganozinc addition; indoline-2,3-diones; pyrazole-4,5-diones.

Abstract

Grants and funding