Synthesis of six-membered spirooxindoles via a chiral Brønsted acid-catalyzed asymmetric intramolecular Friedel–Crafts reaction

Hui-Xuan Chen; Yaqi Zhang; Yuyang Zhang; Xuefeng He; Zhen-Wei Zhang; Hao Liang; Wenhuan He; Xiaoding Jiang; Xiangmeng Chen; Liqin Qiu

doi:10.1039/C8RA06710D

Synthesis of six-membered spirooxindoles via a chiral Brønsted acid-catalyzed asymmetric intramolecular Friedel–Crafts reaction†

Hui-Xuan Chen,^a Yaqi Zhang,^a Yuyang Zhang,^a Xuefeng He,^a Zhen-Wei Zhang,^ab Hao Liang,^a Wenhuan He,^a Xiaoding Jiang,^a Xiangmeng Chen^a and Liqin Qiu

*^a

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* Corresponding authors

^a School of Chemistry, The Key Laboratory of Low-Carbon Chemistry & Energy Conservation of Guangdong Province, South China Sea Bio-Resource Exploitation and Utilization Collaborative Innovation Center, Sun Yat-Sen University, No. 135 Xingangxi Road, Guangzhou 510275, People's Republic of China
E-mail: qiuliqin@mail.sysu.edu.cn
Fax: +86-20-8411-0996

^b College of Pharmacy, Guangxi University of Chinese Medicine, Nanning 530200, People's Republic of China

Abstract

By means of the direct condensation of N-aminoethylpyrroles and isatins, followed by a chiral phosphoric acid-catalyzed asymmetric intramolecular Friedel-Crafts reaction, a new class of valuable chiral 3′,4′-dihydro-2′H-spiro[indoline-3,1′-pyrrolo[1,2-a]pyrazin]-2-ones bearing a quaternary carbon stereocenter were successfully synthesized in good to excellent yields and with moderate to good enantioselectivities under mild reaction conditions.

RSC Advances

Synthesis of six-membered spirooxindoles via a chiral Brønsted acid-catalyzed asymmetric intramolecular Friedel–Crafts reaction†

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Synthesis of six-membered spirooxindoles via a chiral Brønsted acid-catalyzed asymmetric intramolecular Friedel–Crafts reaction

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