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Highly Enantioselective Arylation of N,N-Dimethylsulfamoyl-Protected Aldimines Using Simple Sulfur-Olefin Ligands: Access to Solifenacin and (S)-(+)-Cryptostyline II.
- Source :
-
Organic letters [Org Lett] 2017 Apr 21; Vol. 19 (8), pp. 2138-2141. Date of Electronic Publication: 2017 Apr 07. - Publication Year :
- 2017
-
Abstract
- With the use of a simple sulfur-olefin ligand, a highly enantioselective rhodium-catalyzed addition of arylboroxines to N,N-dimethylsulfamoyl-protected aldimines has been achieved, allowing access to a broad range of chiral diarylmethylamines in high yields (up to 98%) with uniformly excellent enantioselectivities (up to 99% ee). This catalyst system is also applicable to the arylation of N-tosyl arylimines. By utilizing this method, some biologically active molecules possessing a chiral 1-aryl-1,2,3,4-tetrahydroisoquinoline core such as Solifenacin and (S)-(+)-Cryptostyline II are facilely constructed.
Details
- Language :
- English
- ISSN :
- 1523-7052
- Volume :
- 19
- Issue :
- 8
- Database :
- MEDLINE
- Journal :
- Organic letters
- Publication Type :
- Academic Journal
- Accession number :
- 28388063
- Full Text :
- https://doi.org/10.1021/acs.orglett.7b00776