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743585

Sigma-Aldrich

(S)-(−)-1-(2-Diphenylphosphino-1-naphthyl)isoquinoline

≥95.0% (qNMR)

Synonym(s):

(S)-QUINAP

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About This Item

Empirical Formula (Hill Notation):
C31H22NP
CAS Number:
149341-33-3
Molecular Weight:
439.49
Beilstein:
6664856
MDL number:
MFCD01073773
UNSPSC Code:
12352005
PubChem Substance ID:
329765641
NACRES:
NA.22

Assay

≥95.0% (qNMR)

form

crystals

optical purity

enantiomeric excess: ≥98.0%

storage temp.

2-8°C

InChI

1S/C31H22NP/c1-3-13-25(14-4-1)33(26-15-5-2-6-16-26)29-20-19-23-11-7-9-17-27(23)30(29)31-28-18-10-8-12-24(28)21-22-32-31/h1-22H

InChI key

YMJAIEYASUCCMJ-UHFFFAOYSA-N

General description

(S)-QUINAP is a bidentate ligand used in catalytic asymmetric hydroboration, hydrogenation, oxidation, and allylic alkylation reactions.

Application

(S)-QUINAP can be used as a ligand:
  • In the asymmetric hydrosilylation of alkyl and α, β-unsaturated ketones in the presence of Fe(OAc)2.      
  • For the synthesis of chiral organoboron compounds by copper-catalyzed β-borylation of α,β-unsaturated esters.

[Ir(cod)Cl]2 treated with ligand (S)-QUINAP forms an iridium complex. This complex is used as a catalyst for the enantioselective hydrogenation of olefins. (S)-QUINAP–Rh complex can be employed as a catalyst in enantioselective hydroboration/oxidation of perfluoroalkenes.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Practical Preparation and Resolution of 1-(2 `-Diphenylphosphino-1 `-naphthyl) isoquinoline: A Useful Ligand for Catalytic Asymmetric Synthesis
Lim CW, et al.
Organic Process Research & Development, 7(3), 379-384 (2003)
Anna M Segarra et al.
Chemical communications (Cambridge, England), (4), 464-465 (2004-02-07)
Enantioselective access to Markovnikov regioisomeric perfluoroalcohols is achieved in the presence of chiral cationic rhodium complexes and specific hydroborating reagents.
William J Fleming et al.
Organic & biomolecular chemistry, 7(12), 2520-2524 (2009-06-09)
The synthesis and resolution of a new axially chiral Quinazolinap ligand are reported. The application of this and other related P-N ligands to the copper catalyzed beta-borylation of alpha,beta-unsaturated esters resulted in conversions of up to 100% and ee values
Enantioselective hydrogenation of olefins with axial chiral iridium QUINAP complex
Li X, et al.
Tetrahedron Letters, 48(22), 3915-3917 (2007)
Iron-catalyzed enantioselective hydrosilylation of ketones.
Nadim S Shaikh et al.
Angewandte Chemie (International ed. in English), 47(13), 2497-2501 (2008-02-26)

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