CAS 145964-33-6 (R)-(+)-2-Diphenylphosphino-2'-methoxy-1,1'-binaphthyl

IUPAC Name

[1-(2-methoxynaphthalen-1-yl)naphthalen-2-yl]-diphenylphosphane;

Molecular Weight

468.536g/mol

Molecular Formula

C33H25OP;

Canonical SMILES

COC1=C(C2=CC=CC=C2C=C1)C3=C(C=CC4=CC=CC=C43)P(C5=CC=CC=C5)C6=CC=CC=C6;

InChI

InChI=1S/C33H25OP/c1-34-30-22-20-24-12-8-10-18-28(24)32(30)33-29-19-11-9-13-25(29)21-23-31(33)35(26-14-4-2-5-15-26)27-16-6-3-7-17-27/h2-23H,1H3;

InChI Key

KRWTWSSMURUMDE-UHFFFAOYSA-N;

Complexity

634

Covalently-Bonded Unit Count

Exact Mass

468.164g/mol

H-Bond Acceptor

Heavy Atom Count

Monoisotopic Mass

468.164g/mol

Rotatable Bond Count

Topological Polar Surface Area

9.2A^2

Application

(R)-(+)-2-Diphenylphosphino-2'-methoxy-1,1'-binaphthyl, also known as (R)-MOP, serves as a versatile and highly efficient phosphine ligand primarily utilized in catalytic asymmetric reactions. This product is especially valuable in the synthesis of chiral compounds, such as tetrahydrobenzofuranone alkylideneboronates and oxindoles. Furthermore, it plays a critical role in the total synthesis of Oseltamivir Phosphate, a vital antiviral medication targeting influenza virus neuraminidase. The compound's bis-naphthalene backbone enhances its performance as a catalyst in various processes including the hydrosilylation of 1-alkenes, reduction of allylic esters, arylation of imines, and addition of aryl- and alkenylboronic acids to isatins. Additionally, (R)-MOP is used in the desymmetrization of malonamides via an enantioselective intramolecular Buchwald-Hartwig reaction, showcasing its broad applicability and effectiveness in producing optically active molecules.

January 11, 2025

Versatile Catalyst for Asymmetric Synthesis

(R)-(+)-2-Diphenylphosphino-2'-methoxy-1,1'-binaphthyl is an exceptional catalyst. Used it for preparing chiral compounds in my research; its efficiency in asymmetric reactions significantly enhanced our synthesis process. Highly recommend for precise stereochemistry control.