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693537

Sigma-Aldrich

R-MOP

≥94%

Synonym(s):

(R)-(+)-2-(Diphenylphosphino)-2′-methoxy-1,1′-binaphthyl

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About This Item

Empirical Formula (Hill Notation):
C33H25OP
CAS Number:
145964-33-6
Molecular Weight:
468.52
MDL number:
MFCD00269686
UNSPSC Code:
12352005
PubChem Substance ID:
329761598

assay

≥94%

form

solid

optical activity

[α]20/D +94°, c = 0.5 in chloroform

SMILES string

COc1ccc2ccccc2c1-c3c(ccc4ccccc34)P(c5ccccc5)c6ccccc6

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

General description

R-MOP is a phosphine ligand with a bis-naphthalene backbone.

Application

Takasago Ligands and Complexes for Asymmetric Reactions

Ligand used in palladium-catalyzed asymmetric hydrosilylation of olefins, palladium-catalyzed reduction of allylic esters, rhodium-catalyzed asymmetric addition reactions, and asymmetric amination reactions catalyzed by copper(I) complexes.

Legal Information

Sold in collaboration with Takasago for research purposes only. US5231202

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
MKBJ0441V
03502EJ
02704MH

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T Hayashi
Accounts of chemical research, 33(6), 354-362 (2000-07-13)
Chiral monophosphines, whose chirality is due to biaryl axial chirality, have been prepared from enantiomerically pure 2, 2'-dihydroxy-1,1'-binaphthyl and demonstrated to be highly efficient chiral ligands for transition-metal-catalyzed organic transformations, especially for reactions where chelating bisphosphine ligands cannot be used.
The synthesis of P-stereogenic MOP analogues and their use in rhodium catalyzed asymmetric addition
Clarke, E. F.; et al.
Journal of Organometallic Chemistry, 696, 3608-3615 (2011)
Uozomi, Y.
Journal of the American Chemical Society, 9887-9887 (1991)
Rhodium-catalyzed asymmetric addition of aryl- and alkenylboronic acids to isatins.
Ryo Shintani et al.
Angewandte Chemie (International ed. in English), 45(20), 3353-3356 (2006-04-06)
Gaku Hattori et al.
Journal of the American Chemical Society, 132(30), 10592-10608 (2010-07-14)
The scope and limitations of the copper-catalyzed propargylic amination of various propargylic esters with amines are presented, where optically active diphosphines such as Cl-MeO-BIPHEP and BINAP work as good chiral ligands. A variety of secondary amines are available as nucleophiles
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Takasago Ligands

Hydrogenation, Asymmetric Catalysis, Binap, SEGPHOS®, Aldol reaction, Alkenylation, Arylation, Mannich reaction, Fluorination, Michael addition, Hydrosilylation, Cycloaddition, Takasago

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