Enantioselective Michael Addition of 1,3-Diketones to Arenesulfonylalkylindoles: A Flexible Gateway to Optically Active 3-sec-Alkyl-Substituted Indoles Containing a Pyrazole Skeleton

Zongle Zuo; Shilu Zhang; Rongming Wang; Wujun He; Song Wu; Xiaohua Xie; Dabin Qin; Linhai Jing

doi:10.1055/s-0033-1338517

Synthesis, Inhaltsverzeichnis

Synthesis 2013; 45(20): 2832-2842
DOI: 10.1055/s-0033-1338517

paper

Enantioselective Michael Addition of 1,3-Diketones to Arenesulfonylalkylindoles: A Flexible Gateway to Optically Active 3-sec-Alkyl-Substituted Indoles Containing a Pyrazole Skeleton

Authors

Zongle Zuo

^aChemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, China West Normal University, Nanchong 637002, P. R. of China Fax: +86(817)2568081 eMail: jlhhxg@cwnu.edu.cn
Shilu Zhang

^bAnalytical Experimental Center of North Sichuan Medical College, Nanchong 637007, P. R. of China
Rongming Wang

^aChemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, China West Normal University, Nanchong 637002, P. R. of China Fax: +86(817)2568081 eMail: jlhhxg@cwnu.edu.cn
Wujun He

^aChemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, China West Normal University, Nanchong 637002, P. R. of China Fax: +86(817)2568081 eMail: jlhhxg@cwnu.edu.cn
Song Wu

^aChemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, China West Normal University, Nanchong 637002, P. R. of China Fax: +86(817)2568081 eMail: jlhhxg@cwnu.edu.cn
Xiaohua Xie

^aChemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, China West Normal University, Nanchong 637002, P. R. of China Fax: +86(817)2568081 eMail: jlhhxg@cwnu.edu.cn
Dabin Qin

^aChemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, China West Normal University, Nanchong 637002, P. R. of China Fax: +86(817)2568081 eMail: jlhhxg@cwnu.edu.cn
Linhai Jing*

^aChemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, China West Normal University, Nanchong 637002, P. R. of China Fax: +86(817)2568081 eMail: jlhhxg@cwnu.edu.cn

Abstract

Alle Artikel dieser Rubrik

Abstract

Enantioselective Michael addition of 1,3-diketones to alkylideneindolenines generated in situ from arenesulfonylalkylindoles is described, and a series of optically active C3-alkyl-substituted indole derivatives has been obtained. The resulting adducts can be readily converted into 3-sec-alkyl-substituted indoles containing a pyrazole skeleton, with direct connection between the α- and 4-positions, without decrease of the enantioselectivity.

Key words

asymmetric catalysis - Michael addition - arenesulfonylalkylindoles - 1,3-diketones - pyrazoles

Volltext

Referenzen

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