Iridium-catalyzed asymmetric hydroalkynylation reactions of oxabenzonorbornadienes

Jun Hu; Qingjing Yang; Jianbin Xu; Chao Huang; Baomin Fan; Jun Wang; Chengyuan Lin; Zhaoxiang Bian; Albert S. C. Chan

doi:10.1039/C2OB26775F

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Organic & Biomolecular Chemistry

Issue 5, 2013

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Iridium-catalyzed asymmetric hydroalkynylation reactions of oxabenzonorbornadienes

Jun Hu,^a Qingjing Yang,^a Jianbin Xu,^a Chao Huang,^a Baomin Fan,*^a Jun Wang,^b Chengyuan Lin,^b Zhaoxiang Bian^b^c and Albert S. C. Chan*^c

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Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission and Ministry of Education, Yunnan University of Nationalities, Kunming, China
E-mail: adams.bmf@hotmail.com ;
Fax: (+86)-871-5910017

School of Chinese Medicine, Hong Kong Baptist University, Hong Kong, China

Institute of Creativity, Hong Kong Baptist University, Hong Kong, China
E-mail: ascchan@hkbu.edu.hk ;
Fax: +852-34112123

Org. Biomol. Chem., 2013,11, 814-820

DOI: 10.1039/C2OB26775F
Received 10 Sep 2012, Accepted 13 Nov 2012
First published online 13 Nov 2012

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Oxabenzonorbornadienes were found to be suitable substrates for asymmetric hydroalkynylation reactions. Catalyzed by the complex of [Ir(COD)Cl]₂ and (R)-SYNPHOS, oxabenzonorbornadienes and terminal alkynes could react smoothly to give the alkynylated products in moderate to good yields (up to 93% yield) and enantioselectivities (up to 85% ee).

Abstract from Methods in Organic Synthesis 2013

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Jun Hu
Qingjing Yang
Jianbin Xu
Chao Huang
Baomin Fan
Jun Wang
Chengyuan Lin
Zhaoxiang Bian
Albert S. C. Chan

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