Journal
ACS CATALYSIS
Volume 9, Issue 8, Pages 6890-6895Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.9b02080
Keywords
allenes; copper; enantioselectivity; boroacylation; quaternary stereocenter
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Funding
- NSFC [21425205, 21672067]
- 973 Program [2015CB856600]
- Program for Changjiang Scholars and Innovative Research Team [IRT-16R25]
- Program of Eastern Scholar at Shanghai Institutions of Higher Learning
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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.
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