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905305

Sigma-Aldrich

(S,S,S)-SPIRAP

≥95%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C43H38O2P2
Molecular Weight:
648.71

Assay

≥95%

form

powder or crystals

reaction suitability

reaction type: Asymmetric synthesis
reagent type: ligand

mp

226-228 °C

functional group

phosphine

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

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.

Product can be used with our benchtop hydrogen generator, H-Genie Lite (Z744083)

Other Notes

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

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Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Alonso J Argüelles et al.
Angewandte Chemie (International ed. in English), 57(19), 5325-5329 (2018-02-24)
We present an expedient and economical route to a new spiroketal-based C2 -symmetric chiral scaffold, termed SPIROL. Based on this spirocyclic scaffold, several chiral ligands were generated. These ligands were successfully employed in an array of stereoselective transformations, including in
Design, Synthesis, and Application of Chiral C2-Symmetric Spiroketal-Containing Ligands in Transition-Metal Catalysis.
Arguelles AJ, et al.
Angewandte Chemie (International Edition in English), 57(19), 5325-5329 (2018)

Related Content

Nagorny Group - Professor Product Portal

The Nagorny group has designed a new class of spiroketal-based chiral scaffolds termed SPIROLs. The SPIROL-based ligands have demonstrated excellent performance in a variety of Pd-, Rh- and Ir-catalyzed transformations while being easily accessible. Other focus areas are asymmetric catalysis, chiral catalyst, ligand design, which are all dedicated to the development of immobilized organic catalysts.

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