Stereoselective Synthesis of Polysubstituted Dihydropyrroles via 1,5-Addition and N-1,4-Addition Cascade

Jing-Ming Zhang; Yu-Chao Wang; Liang Chen; Chao Ma; Zhi-Tao He

doi:10.1002/chem.202401350

Stereoselective Synthesis of Polysubstituted Dihydropyrroles via 1,5-Addition and N-1,4-Addition Cascade

Chemistry. 2024 Jul 5;30(38):e202401350. doi: 10.1002/chem.202401350. Epub 2024 Jun 12.

Authors

Jing-Ming Zhang^{1

2}, Yu-Chao Wang², Liang Chen^{1

2}, Chao Ma², Zhi-Tao He^{1

2

3}

Affiliations

¹ School of Chemistry and Materials Science, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, 310024, Hangzhou, China.
² State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, 200032, Shanghai, China.
³ Ningbo Zhongke Creation Center of New Materials, 315899, Ningbo, China.

PMID: 38700514
DOI: 10.1002/chem.202401350

Abstract

An unprecedented 1,5-addition/N-1,4-addition cascade reaction is established via palladium hydride catalysis. A variety of polysubstituted dihydropyrrole skeletons are constructed in high yield and with exclusively >20 : 1 diastereoselectivity. An enantioselective protocol of this design is also developed to provide a novel access to enantioenriched dihydropyrroles.

Keywords: 1,5-addition; N-1,4-addition; enantioselective; palladium hydride; stereoselective.

Abstract

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