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Merck
CN

905240

(R,R,R)-SPIRAP

≥95%, powder or crystals

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C43H38O2P2
Molecular Weight:
648.71
MDL number:
MFCD32062477
UNSPSC Code:
12161600
NACRES:
NA.22

Key Documents

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Product Name

(R,R,R)-SPIRAP, ≥95%

InChI

1S/C43H38O2P2/c1-3-37-35-27-17-29-39(46(31-19-9-5-10-20-31)32-21-11-6-12-22-32)41(35)43(44-37)42-36(38(4-2)45-43)28-18-30-40(42)47(33-23-13-7-14-24-33)34-25-15-8-16-26-34/h5-30,37-38H,3-4H2,1-2H3/t37-,38-,43-/m1/s1

InChI key

PRORVWYPBRMLLA-FFUXEPPCSA-N

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

assay

≥95%

form

powder or crystals

reaction suitability

reagent type: ligand
reaction type: Asymmetric synthesis

mp

226-228 °C

Related Categories

Application

(R,R,R)-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

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKCJ2892

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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

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Nagorny group designs SPIROL-based ligands for efficient catalysis, focusing on asymmetric transformations.

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