CAS 500997-70-6 (Sa,R,R)-SIPHOS-PE - Catalysts / Alfa Chemistry

Synonyms

500997-69-3; (11aS)-(-)-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; (11AR)-(+)-10,11,12,13-TETRAHYDRODIINDENO[7,1-DE:1',7'-FG][1,3,2]DIOXAPHOSPHOCIN-5-BIS(R)-1PHENYLETHYL]AMINE; (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; 997S693; SCHEMBL19695663; RT-015574; CTK8E6816; (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; (S)-SIPHOS-PE;

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

(Sa,R,R)-SIPHOS-PE serves as a versatile chiral spiro phosphoramidate ligand designed to facilitate a wide range of catalytic asymmetric transformations. Its applications include the synthesis of spiroindolenines through palladium-catalyzed intramolecular dearomative arylation of haloaryl-3-substituted indoles, and the formation of enantioselective conjugate addition compounds by copper-catalyzed 1,4-addition of diethylzinc to cyclic enones. It also aids in the creation of octaketide natural products via rhodium-phosphoramidite-catalyzed alkene hydroacylation. Furthermore, (Sa,R,R)-SIPHOS-PE is used in copper-catalyzed asymmetric allylic alkylation with dialkylzincs, palladium-catalyzed asymmetric hydrosilylation of styrenes, copper-catalyzed asymmetric ring-opening of oxabicyclic alkenes with Grignard reagents, and nickel-catalyzed asymmetric hydrovinylation of α-alkyl vinylarenes. Additionally, it supports iridium-catalyzed asymmetric hydrogenation of cyclic enamines and cyclic imines. The ligand also finds use in gold-catalyzed asymmetric [2 + 2] cycloaddition reactions, rhodium-catalyzed asymmetric hydroacylation of salicylaldehydes to homoallylic sulfides, and palladium-catalyzed asymmetric carboamination reactions, making it an essential tool in asymmetric synthesis.

January 3, 2025

Exceptional Performance in Complex Syntheses

After incorporating (Sa,R,R)-SIPHOS-PE from Alfa Chemistry in our lab, our research efficiency improved significantly. It's excellent for Pd-catalyzed arylation and Cu-catalyzed additions, making complex operations seamless and precise. Truly a game-changer in chiral synthesis.