1392835-27-6

Basic information

• Product Name: (R)-(2-chlorophenyl)(4-methoxyphenyl)methanol
• Synonyms: (R)-(2-chlorophenyl)(4-methoxyphenyl)methanol
• CAS NO: 1392835-27-6
• Molecular Weight: 248.709
• Mol File: 1392835-27-6.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (R)-(2-chlorophenyl)(4-methoxyphenyl)methanol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(2-chlorophenyl)(4-methoxyphenyl)methanol(1392835-27-6)
• EPA Substance Registry System: (R)-(2-chlorophenyl)(4-methoxyphenyl)methanol(1392835-27-6)

Safety Data

• Hazardous Substances Data: 1392835-27-6(Hazardous Substances Data)

Upstream product

• 104-93-8 p-methylanizole 
• 609-65-4 o-chlorobenzoyl chloride 
• 54118-74-0 2-chloro-4'-methoxybenzophenone 
• 89-98-5 2-chloro-benzaldehyde 
• 13139-86-1 4-methoxyphenyl magnesium bromide 

Relevant articles and documents

Synthesis of Ar-BINMOL ligands by [1,2]-wittig rearrangement to probe their catalytic activity in 1,2-addition reactions of aldehydes with Grignard reagents

We have demonstrated a highly diastereoselective synthesis of optically pure Ar-BINMOL-derived diols and their analogues. The present study demonstrates a unique cascade chirality transfer in a [1,2]-Wittig rearrangement that leads to chiral diols with three stereogenic centers, which include a chiral sp 3 center at the alcohol and C2-axial chirality. Screening these ligands in the arylation of aromatic aldehydes with Grignard reagents shows that the naphthyl-substituted BINMOL promotes the aryl transfer reaction in good yields (70-92 %) and moderate-to-good enantioselectivities (up to 72 % ee), and a series of control experiments substantiates that the axial chirality and the chiral sp3 center at the alcohol of the Ar-BINMOLs are the pivotal enantioselectivity-controlling structure elements. In addition, this study demonstrated the importance of the chiral sp3 center at the alcohol on Ar-BINMOL for the aryl transfer reaction. Finally, we found that the chiral Ar-BINMOL ligand 2h mediated the titanium-promoted 1,2-addition of MeMgBr to aldehydes to give the desired products in good yields with excellent enantioselectivities (up to 92 % ee). Ar-BINMOL ligands: A new diastereoselective synthesis of optically pure Ar-BINMOL-derived diols and their analogues has been established through cascade chirality transfer of a [1,2]-Wittig rearrangement. The axial and sp3 central chirality of Ar-BINMOLs are the pivotal enantioselectivity-controlling structure elements in the 1,2-addition of aldehydes with Grignard reagents. Copyright