4.8 Article

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

Journal

ACS CATALYSIS
Volume 9, Issue 8, Pages 6890-6895

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acscatal.9b02080

Keywords

allenes; copper; enantioselectivity; boroacylation; quaternary stereocenter

Funding

  1. NSFC [21425205, 21672067]
  2. 973 Program [2015CB856600]
  3. Program for Changjiang Scholars and Innovative Research Team [IRT-16R25]
  4. 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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