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Synthesis 2020; 52(10): 1498-1511
DOI: 10.1055/s-0037-1610749
DOI: 10.1055/s-0037-1610749
paper
Highly Enantioselective Rh-Catalyzed Arylation of N,N-Dimethylsulfamoyl-Protected Aldimines and Cyclic N-Sulfonylimines with Chiral Phenyl Backbone Sulfoxide-Olefin Ligands
National Natural Science Foundation of China (21172218)Further Information
Publication History
Received: 12 November 2019
Accepted after revision: 17 January 2020
Publication Date:
10 February 2020 (online)
Abstract
With chiral 2-methoxy-1-naphthylsulfinyl-based phenyl backbone sulfoxide-olefin ligands, a highly Rh-catalyzed addition of arylboronic acids to N,N-dimethylsulfamoyl-protected aldimines has been developed to afford a broad range of chiral diarylmethylamines in high yields (up to 99%) with excellent enantioselectivities (up to 99% ee). Moreover, efficient enantioselective arylation of cyclic N-sulfonylimines was also achieved with excellent enantioselectivities (up to 98% ee).
Key words
arylation - arylboronic acids - N,N-dimethylsulfamoyl-protected aldimines - sulfoxide-olefin ligands - asymmetric catalysisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610749.
- Supporting Information
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For reviews, see:
For other representative bis-sulfoxide examples, see:
For representative sulfoxide-phosphine examples, see:
For representative sulfoxide-olefin examples, see:
For representative examples, see:
For representative examples, see:
For representative examples on catalytic rhodium-catalyzed arylations of N-tosyl or -nosyl activated/protected imines with arylboron reagents, see: