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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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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
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.
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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