CAS 500997-69-3 (Ra,R,R)-SIPHOS-PE - Catalysts / Alfa Chemistry

Synonyms

SCHEMBL17227906; (S)-SIPHOS-PE; Diindeno[7,1-de:1',7'-fg][1,3,2]dioxaphosphocin-5-amine,10,11,12,13-tetrahydro-N,N-bis[(1R)-1-phenylethyl]-, (11aR)-; N-Di[(R)-1-phenylethyl]-[(S)-1,1 inverted exclamation marka-spirobiindane-7,7 inverted exclamation marka-diyl]-phosphoramidite; N-Di[(R)-1-phenylethyl]-[(R)-1,1 inverted exclamation marka-spirobiindane-7,7 inverted exclamation marka-diyl]-phosphoramidite; AKOS015950899; (11aR)-(+)-10,11,12,13-Tetrahydrodiindeno[7,1-de:1, 7-fg][1,3,2]dioxaphosphocin-5-bis[(R)-1-phenylethyl]amine,N-Di[(R)-1-phenylethyl]-[(R)-1,1-spirobiindane-7,7-diyl]-phosphoramidite; (11aR)-(+)-10,11,12,13-Tetrahydrodiindeno[7,1-de:1 inverted exclamation marka, 7 inverted exclamation marka-fg][1,3,2]dioxaphosphocin-5-bis[(R)-1-phenylethyl]amine; RT-015574; CTK8E6816;

IUPAC Name

N,N-bis[(1R)-1-phenylethyl]-4,5,6,7-tetrahydroiindeno[7,1-de:1',7'-fg][1,3,2]dioxaphosphocin-12-amine;

Molecular Weight

505.598g/mol

Molecular Formula

C33H32NO2P;

Canonical SMILES

CC(C1=CC=CC=C1)N(C(C)C2=CC=CC=C2)P3OC4=CC=CC5=C4C6(CC5)CCC7=C6C(=CC=C7)O3;

InChI

InChI=1S/C33H32NO2P/c1-23(25-11-5-3-6-12-25)34(24(2)26-13-7-4-8-14-26)37-35-29-17-9-15-27-19-21-33(31(27)29)22-20-28-16-10-18-30(36-37)32(28)33/h3-18,23-24H,19-22H2,1-2H3/t23-,24-,33 /m1/s1;

InChI Key

ZXLQLIDJAURBDD-HRPAVAKOSA-N;

Complexity

716

Covalently-Bonded Unit Count

Defined Atom Stereocenter Count

Exact Mass

505.217g/mol

H-Bond Acceptor

Heavy Atom Count

Monoisotopic Mass

505.217g/mol

Rotatable Bond Count

Topological Polar Surface Area

21.7A^2

Application

(Ra,R,R)-SIPHOS-PE serves as a versatile chiral ligand and catalyst for an array of chemical transformations. It finds application in the preparation of tricyclic alkaloid (+)-aphanorphine through asymmetric carboamination and Friedel-Crafts reactions. Additionally, it is used in the synthesis of chiral ketones via hydroacylation of olefins with salicylaldehyde derivatives and in the enantioselective production of substituted pyrrolidine derivatives through Pd-catalyzed alkene aminoarylation reactions. The compound is also employed as a chiral ligand in copper-catalyzed asymmetric allylic alkylation with dialkylzincs, conjugate addition of diethylzinc to enones, and ring-opening of oxabicyclic alkenes using Grignard reagents. Furthermore, it plays a role in palladium-catalyzed asymmetric hydrosilylation of styrenes and asymmetric carboamination reactions. Its versatility extends to nickel-catalyzed asymmetric hydrovinylation of α-alkyl vinylarenes, iridium-catalyzed asymmetric hydrogenation of cyclic enamines and imines, as well as gold-catalyzed asymmetric [2 + 2] cycloaddition reactions. Lastly, it is involved in rhodium-catalyzed asymmetric hydroacylation of salicylaldehydes to form homoallylic sulfides.

January 14, 2025

Efficient Catalyst for Advanced Chiral Synthesis

I've been using (Ra,R,R)-SIPHOS-PE in my research for asymmetric synthesis. It's exceptional as a chiral ligand in palladium-catalyzed reactions, significantly enhancing enantioselectivity in synthesizing complex chiral structures. Highly recommend it!