Palladium-catalyzed intermolecular [4 + 2] formal cycloaddition with (Z)-3-iodo allylic nucleophiles and allenamides

Fachao Yan; Hanbing Liang; Bing Ai; Wenjing Liang; Luyang Jiao; Shuzhi Yao; Pingping Zhao; Qing Liu; Yunhui Dong; Hui Liu

doi:10.1039/C8OB03072C

Palladium-catalyzed intermolecular [4 + 2] formal cycloaddition with (Z)-3-iodo allylic nucleophiles and allenamides†

Fachao Yan,‡^a Hanbing Liang,‡^a Bing Ai,^a Wenjing Liang,^a Luyang Jiao,^a Shuzhi Yao,^a Pingping Zhao,^b Qing Liu,*^a Yunhui Dong^a and Hui Liu

*^a

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* Corresponding authors

^a School of Chemistry and Chemical Engineering, Shandong University of Technology, 266 West Xincun Road, Zibo 255049, P. R. China
E-mail: huiliu1030@sdut.edu.cn

^b College of Chemical and Environmental Engineering, Shandong University of Science and Technology, 579 Qianwangang Road, Qingdao, Huangdao District, P. R. China

Abstract

A highly chemo- and regioselective [4 + 2] formal cycloaddition of (Z)-3-iodo allylic nucleophiles and allenamides catalyzed by palladium is reported. The methodology proceeds under mild reaction conditions and is tolerant of alkyl and aryl functional groups. The S_N2′ substitution at the proximal C [double bond, length as m-dash] C bond performed against the Heck or S_N2 pathway delivered a variety of 2-amino-dihydropyrans and 2-amino-tetrahydropiperidines in moderate to satisfactory yields. The [4 + 2] formal cycloaddition derivatives are convertible to interesting scaffolds 2,6,7,7a-tetrahydropyrano[2,3-b]pyrrole and 2,6,7,7a-tetrahydro-1H-pyrrolo[2,3-b]pyridine derivatives via ring-closing metathesis (RCM) with Grubbs catalyst II.

Organic & Biomolecular Chemistry

Palladium-catalyzed intermolecular [4 + 2] formal cycloaddition with (Z)-3-iodo allylic nucleophiles and allenamides†

Abstract

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Palladium-catalyzed intermolecular [4 + 2] formal cycloaddition with (Z)-3-iodo allylic nucleophiles and allenamides

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