Chiral-Boron Complex-Catalyzed Asymmetric [3 + 2] Cycloaddition of 2′-Hydroxychalcones with N‑2,2,2-Trifluoroethylisatin Ketimines

A highly efficient asymmetric [3 + 2] cycloaddition reaction of 2′-hydroxychalcones with N-2,2,2-trifluoroethylisatin ketimines catalyzed by a (R)-3,3′-I2-BINOL-boron complex was developed. A broad range of 3,2′-pyrrolidinyl spirooxindole derivatives bearing a CF3-substituted pyrrolidine moiety with...

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Veröffentlicht in:	Journal of organic chemistry 2024-08, Vol.89 (16), p.11607-11619
Hauptverfasser:	Chai, Guo-Li, Wang, Xiao, Huang, Wei-Yu, Hou, Ya-Jing, Chang, Junbiao
Format:	Artikel
Sprache:	eng
Schlagworte:	cycloaddition reactions ketimines moieties organic chemistry
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container_end_page	11619
container_issue	16
container_start_page	11607
container_title	Journal of organic chemistry
container_volume	89
creator	Chai, Guo-Li Wang, Xiao Huang, Wei-Yu Hou, Ya-Jing Chang, Junbiao
description	A highly efficient asymmetric [3 + 2] cycloaddition reaction of 2′-hydroxychalcones with N-2,2,2-trifluoroethylisatin ketimines catalyzed by a (R)-3,3′-I2-BINOL-boron complex was developed. A broad range of 3,2′-pyrrolidinyl spirooxindole derivatives bearing a CF3-substituted pyrrolidine moiety with four contiguous stereocenters was prepared in high yields with excellent diastereo- and enantioselectivities (up to >20:1 dr and >99% ee). This protocol had the characteristics of mild reaction conditions, high efficiency, and excellent stereocontrol.
doi_str_mv	10.1021/acs.joc.4c01319
format	Article
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Org. Chem</addtitle><date>2024-08-01</date><risdate>2024</risdate><volume>89</volume><issue>16</issue><spage>11607</spage><epage>11619</epage><pages>11607-11619</pages><issn>0022-3263</issn><issn>1520-6904</issn><eissn>1520-6904</eissn><abstract>A highly efficient asymmetric [3 + 2] cycloaddition reaction of 2′-hydroxychalcones with N-2,2,2-trifluoroethylisatin ketimines catalyzed by a (R)-3,3′-I2-BINOL-boron complex was developed. A broad range of 3,2′-pyrrolidinyl spirooxindole derivatives bearing a CF3-substituted pyrrolidine moiety with four contiguous stereocenters was prepared in high yields with excellent diastereo- and enantioselectivities (up to >20:1 dr and >99% ee). 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subjects	cycloaddition reactions ketimines moieties organic chemistry
title	Chiral-Boron Complex-Catalyzed Asymmetric [3 + 2] Cycloaddition of 2′-Hydroxychalcones with N‑2,2,2-Trifluoroethylisatin Ketimines
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