1809609-53-7

Basic information

• Product Name: (R)-N-((3-Methylpyridin-2-yl)methyl)-7′-di(3,5-di-tert-butylphenyl)phosphino-1,1′-spirobiindanyl-7-amine
• Synonyms: (R)-DTB-SpiroSAP
• CAS NO: 1809609-53-7
• Molecular Formula: C50H66NPS2
• Molecular Weight: 776.169501
• Product Categories: Chiral Phosphine;Chiral Spiro Ligand
• Mol File: 1809609-53-7.mol
• Article Data: 1

Chemical Properties

• Melting Point: 95-97°C
• Appearance: white to off-white/solid
• Sensitive: air sensitive
• CAS DataBase Reference: (R)-N-((3-Methylpyridin-2-yl)methyl)-7′-di(3,5-di-tert-butylphenyl)phosphino-1,1′-spirobiindanyl-7-amine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-N-((3-Methylpyridin-2-yl)methyl)-7′-di(3,5-di-tert-butylphenyl)phosphino-1,1′-spirobiindanyl-7-amine(1809609-53-7)
• EPA Substance Registry System: (R)-N-((3-Methylpyridin-2-yl)methyl)-7′-di(3,5-di-tert-butylphenyl)phosphino-1,1′-spirobiindanyl-7-amine(1809609-53-7)

Safety Data

• Hazardous Substances Data: 1809609-53-7(Hazardous Substances Data)

Usage

Reaction

Chiral P-N-S Spiro Ligand used in the Iridium-catalyzed asymmetric Hydrogenation of Ketoesters.

Upstream product

• 109-80-8 1.3-propanedithiol 
• 1219025-18-9 (R)-7′-bis-(3,5-di-tert-butylphenyl)phosphino-7′-amino-1,1′-spiroindene 

Relevant articles and documents

Development of Chiral Spiro P-N-S Ligands for Iridium-Catalyzed Asymmetric Hydrogenation of β-Alkyl-β-Ketoesters

The chiral tridentate spiro P-N-S ligands (SpiroSAP) were developed, and their iridium complexes were prepared. Introduction of a 1,3-dithiane moiety into the ligand resulted in a highly efficient chiral iridium catalyst for asymmetric hydrogenation of β-alkyl-β-ketoesters, producing chiral β-alkyl-β-hydroxyesters with excellent enantioselectivities (95-99.9 % ee) and turnover numbers of up to 355 000. Bulkyness is the key: New chiral tridentate spiro P-N-S ligands (SpiroSAP) bearing a conformationally constrained 1,3-dithiane moiety were developed. Their iridium catalysts showed excellent enantioselectivities and activity (TON up to 355 000) for asymmetric hydrogenation of β-alkyl-β-ketoesters.