Design and Synthesis of WJ-Phos, and Application in Cu-Catalyzed Enantioselective Boroacylation of 1,1-Disubstituted Allenes

The highly enantioselective copper-catalyzed three-component boroacylation of 1,1-disubstituted allenes is reported by using a class of chiral ligands (WJ-Phos), delivering various functionalized organoboron compounds bearing an all-carbon stereocenter in moderate to good yields with high enantiosel...

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Veröffentlicht in:ACS catalysis 2019-08, Vol.9 (8), p.6890-6895
Hauptverfasser: Han, Jie, Zhou, Wei, Zhang, Pei-Chao, Wang, Huamin, Zhang, Ronghua, Wu, Hai-Hong, Zhang, Junliang
Format: Artikel
Sprache:eng
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Zusammenfassung:The highly enantioselective copper-catalyzed three-component boroacylation of 1,1-disubstituted allenes is reported by using a class of chiral ligands (WJ-Phos), delivering various functionalized organoboron compounds bearing an all-carbon stereocenter in moderate to good yields with high enantioselectivities. WJ-Phos is a ferrocene-derived chiral sulfinamide phosphine ligand and can be easily synthesized in gram-scale from readily available starting materials in short steps. The salient features of this reaction include moderate to good yields, high enantioselectivities, gram-scale synthesis, diverse synthetic transformations, and the development of a new chiral ligand.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.9b02080