898231-59-9

Basic information

• Product Name: (R)-N-((4-chlorophenyl)(phenyl)methyl)-N’,N’-dimethylsulfamide
• Synonyms: (R)-N-((4-chlorophenyl)(phenyl)methyl)-N’,N’-dimethylsulfamide
• CAS NO: 898231-59-9
• Molecular Weight: 324.831
• Mol File: 898231-59-9.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (R)-N-((4-chlorophenyl)(phenyl)methyl)-N’,N’-dimethylsulfamide(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-N-((4-chlorophenyl)(phenyl)methyl)-N’,N’-dimethylsulfamide(898231-59-9)
• EPA Substance Registry System: (R)-N-((4-chlorophenyl)(phenyl)methyl)-N’,N’-dimethylsulfamide(898231-59-9)

Safety Data

• Hazardous Substances Data: 898231-59-9(Hazardous Substances Data)

Upstream product

• 898231-16-8 N,N-dimethyl-N'-[(4-chlorophenyl)methylene]sulfamide 
• 98-80-6 phenylboronic acid 
• 104-88-1 4-chlorobenzaldehyde 
• 3262-89-3 triphenylboroxine 
• 940939-32-2 (E)-N-(4-chlorobenzylidene)-N’,N’-dimethylsulfamide 
• 7519-91-7 tris(4-chlorophenyl)boroxine 
• 118847-62-4 N,N-dimethyl-N'-(phenylmethylene)sulfamide 

Downstream Products

• 163837-57-8 (R)-(4-chlorophenyl)(phenyl)methylamine 

Relevant articles and documents

Highly Enantioselective Arylation of N,N-Dimethylsulfamoyl-Protected Aldimines Using Simple Sulfur-Olefin Ligands: Access to Solifenacin and (S)-(+)-Cryptostyline II

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.

Highly Enantioselective Ferrocenyl Palladacycle-Acetate Catalysed Arylation of Aldimines and Ketimines with Arylboroxines

Benzylic N-substituted stereocenters constitute a frequent structural motif in drugs. Their highly enantioselective generation is hence of technical importance. An attractive strategy is the arylation of imines with organoboron reagents. Chiral Rh complexes have reached a high level of productivity for this reaction type. In this article we describe that an electron rich PdIIcatalyst also performs well in the arylation of aldimines, comparable to the best Rh catalysts. The ferrocenyl palladacycle-acetate catalyst allows for a broad substrate scope and very high enantioselectivities. Commonly observed side reactions like aryl–aryl homocouplings and imine hydrolysis could be blocked. Mechanistic studies implicate that a) the acetate ligand is crucial for transmetallation, b) the active catalyst is most likely a palladacycle-OAc monomer, c) the rate limiting step is probably the product release. By added KOAc the arylation could also be applied to ketimines.

A ligand-library approach to the highly efficient rhodium/phosphoramidite- catalyzed asymmetric arylation of N,N-dimethylsulfamoyl-protected aldimines

(Chemical Equation Presented) Small but effective: The title reaction, after microwave-assisted removal of the N,N-dimethylsulfamoyl protecting group, leads to chiral diarylmethyl amines. The use of 1 mol% catalyst and 1.3 equivalents of aryl boronic acid results in excellent yields (up to 98%) and enantioselectivities (up to 95% ee) of the isolated products. acac = acetylacetonate; eth = ethylene.