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Chiral Phosphine Ligands
(+)-1,2-BIS((2S,5S)-2,5-DIPHENYLPHOSPHOLANO)ETHANE

(+)-1,2-BIS((2S,5S)-2,5-DIPHENYLPHOSPHOLANO)ETHANE - CAS 824395-67-7

(+)-1,2-BIS((2S,5S)-2,5-DIPHENYLPHOSPHOLANO)ETHANE is a chiral phosphine ligand for enantioselective synthesis with high yield and high enantioselective results.

Catalog Number

824395-67-7

CAS

824395-67-7

IUPAC Name

(2S,5S)-1-[2-[(2S,5S)-2,5-diphenylphospholan-1-yl]ethyl]-2,5-diphenylphospholane

Synonyms

(+)-1,2-BIS((2S,5S)-2,5-DIPHENYLPHOSPHOLANO)ETHANE; (+)-1,2-BIS((2S,5S)-2,5-DIPHENYLPHOSPHOLANO)ETHANE, KANATA PURITY; (+)-1,2-Bis((2S,5S)-2,5-diphenylphospholano)ethane,min.98%(S,S)-Ph-BPE

Application

(+)-1,2-Bis((2S,5S)-2,5-diphenylphospholano)ethane is a potentially useful synthetic intermediate

Molecular Weight

506.6

Molecular Formula

C34H36P2

Product Information

Canonical SMILES

C1C[C@H](P(CCP2[C@@H](CC[C@H]2c3ccccc3)c4ccccc4)[C@@H]1c5ccccc5)c6ccccc6

InChI

InChI=1S/C34H36P2/c1-5-13-27(14-6-1)31-21-22-32(28-15-7-2-8-16-28)35(31)25-26-36-33(29-17-9-3-10-18-29)23-24-34(36)30-19-11-4-12-20-30/h1-20,31-34H,21-26H2/t31-,32-,33-,34-/m0/s1

InChI Key

VHHAZLMVLLIMHT-CUPIEXAXSA-N

Purity

95%

MDL

MFCD07369028

Physical State

Solid

Storage

Inert atmosphere. Keep cold.

Melting Point

144°C

Solubility

Sparingly Soluble (3.2E-5 g/L) (25 °C).

TSCA

WGK Germany

Safety Information

Signal Word

Warning

Precautionary Statement

P261 - P280 - P301+P312 - P302+P352 - P305+P351+P338

Hazard Statements

H302 - H315 - H319 - H335

Reference Reading

1.Rapid Asymmetric Transfer Hydroformylation (ATHF) of Disubstituted Alkenes Using Paraformaldehyde as a Syngas Surrogate.

Fuentes JA1, Pittaway R1, Clarke ML2. Chemistry. 2015 Jul 20;21(30):10645-9. doi: 10.1002/chem.201502049. Epub 2015 Jun 25.

As an alternative to conventional asymmetric hydroformylation (AHF), asymmetric transfer hydroformylation (ATHF) by using formaldehyde as a surrogate for syngas is reported. A catalyst derived from commercially available [Rh(acac)(CO)2 ] (acac=acetylacetonate) and 1,2-bis[(2S,5S)-2,5-diphenylphospholano]ethane(1,5-cyclooctadiene) (Ph-BPE) stands out in terms of both activity and enantioselectivity. Remarkably, not only are high selectivities achievable, the reactions are very simple to perform, and higher enantioselectivity (up to 96 % ee) and/or turnover frequencies than those achievable by using the same catalyst (or other leading catalysts) can be obtained by using typical conditions for AHF.

The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass