Synthesis 2018; 50(05): 1105-1112
DOI: 10.1055/s-0036-1590955
paper
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Chlorination of Cyclic β-Keto Esters and N-Boc Oxindoles­ Catalyzed by an Iron(III)-BPsalan Complex

Yong-Heng Luo
a   School of Chemical and Environmental Engineering, Shanghai Institute of Technology, 100 Haiquan Road, Shanghai, P. R. of China
,
Yuan-Ji Ping
b   Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, 354 Feng Lin Road, Shanghai 200032, P. R. of China   eMail: xuzhenjiang@sioc.ac.cn
,
Zong-Rui Li
b   Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, 354 Feng Lin Road, Shanghai 200032, P. R. of China   eMail: xuzhenjiang@sioc.ac.cn
,
Xin Gu
b   Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, 354 Feng Lin Road, Shanghai 200032, P. R. of China   eMail: xuzhenjiang@sioc.ac.cn
,
Zhen-Jiang Xu*
b   Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, 354 Feng Lin Road, Shanghai 200032, P. R. of China   eMail: xuzhenjiang@sioc.ac.cn
,
Chi-Ming Che*
b   Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, 354 Feng Lin Road, Shanghai 200032, P. R. of China   eMail: xuzhenjiang@sioc.ac.cn
c   Department of Chemistry and State Key Laboratory of Synthetic Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, SAR, P. R. of China   eMail: cmche@hku.hk
› Institutsangaben
We thank the National Natural Science Foundation of China (NSFC 21472216) and the Croucher Funding Scheme for Joint laboratories for financial support.
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Publikationsverlauf

Received: 29. August 2017

Accepted after revision: 12. Oktober 2017

Publikationsdatum:
09. November 2017 (online)


Abstract

An iron(III)-BPsalan complex was found to efficiently catalyze the asymmetric chlorination reaction of cyclic β-keto esters and N-Boc oxindoles, affording the corresponding chlorinated products in high yield and up to 92% ee with NCS as chlorination reagent under mild reaction conditions.

Supporting Information