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905305 Sigma-Aldrich

(S,S,S)-SPIRAP

≥95%

Synonym: ((1S,3S,3′S)-3,3′-diethyl-3H,3′H-1,1′-spirobi[isobenzofuran]-7,7′-diyl)bis(diphenylphosphane), (S)-CrabPhos

  • Empirical Formula (Hill Notation) C43H38O2P2

  • Molecular Weight 648.71

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Privileged Ligands and Complexes, Spiro Ligands More...
assay   ≥95%
form   powder or crystals
reaction suitability   reaction type: Asymmetric synthesis
mp   226-228 °C
SMILES string   CC[C@H](O1)C2=C([C@@]1(O[C@@H]3CC)C4=C3C=CC=C4P(C5=CC=CC=C5)C6=CC=CC=C6)C(P(C7=CC=CC=C7)C8=CC=CC=C8)=CC=C2

Description

Application

(S,S,S)-SPIRAP is a chiral C2-symmetric spiroketal-containing ligand developed in the Nagorny lab for asymmetric catalysis. It can be used in variety of stereoselective transformations, including: Ir-catalyzed hydroarylation, Pd-catalyzed allylic alkylation, Pd-catalyzed Heck couplings, and Rh-catalyzed hydrogenation.

Other Notes

Design, Synthesis, and Application of Chiral C2-Symmetric Spiroketal-Containing Ligands in Transition-Metal Catalysis

Safety & Documentation

Safety Information

WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

Professor Product Portal - Nagorny Group

From our library of Articles, Sigma-Aldrich presents Professor Product Portal - Nagorny Group
Keywords: Asymmetric catalysis, Asymmetric synthesis, Catalysis, Diseases, Glycosylations, Hydrogenations, Immobilization, Infrared spectroscopy, Ligands, Organic synthesis

Peer-Reviewed Papers
15

References

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