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905356

Sigma-Aldrich

Rh2(R-PTAD)4

Synonym(s):

Tetrakis[(R)-(-)-(1-adamantyl)-(N-phthalimido)acetato]dirhodium(II)

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About This Item

Empirical Formula (Hill Notation):
C80H80N4O16Rh2
CAS Number:
909393-65-3
Molecular Weight:
1559.32
MDL number:
MFCD09839139
UNSPSC Code:
12161600
NACRES:
NA.22

form

powder or crystals

mp

>300 °C

SMILES string

[Rh]([Rh](OC(=O)[C@H](N%19C(=O)c%20c(cccc%20)C%19=O)C%17%16C[C@@H]%18C[C@@H](C[C@@H](C%18)C%17)C%16)OC(=O)[C@H](N%14C(=O)c%15c(cccc%15)C%14=O)C%12%11C[C@@H]%13C[C@@H](C[C@@H](C%13)C%12)C%11)(OC(=O)[C@H](N9C(=O)c%10c(cccc%10)C9=O)C76C[C@@H]8C[C@@H](C[C@@H]

InChI

1S/4C20H21NO4.2Rh/c4*22-17-14-3-1-2-4-15(14)18(23)21(17)16(19(24)25)20-8-11-5-12(9-20)7-13(6-11)10-20;;/h4*1-4,11-13,16H,5-10H2,(H,24,25);;/q;;;;2*+2/p-4/t4*11-,12+,13-,16-,20?;;/m0000../s1

InChI key

SGEDWOHAUXKUGM-VMLWFVNWSA-J

Application

This chiral Rh(II) dimer was developed in the Davies lab to perform asymmetric carbene and nitrene reactions (C-H insertion, cyclopropanation, aziridination, C-H amination) with high regio- and stereo-control.

Other Notes

Dirhodium Tetracarboxylate Derived from Adamantylglycine as a Chiral Catalyst for Carbenoid Reactions

Asymmetric Synthesis of Tropanes by Rhodium-Catalyzed [4 + 3] Cycloaddition

Asymmetric [4 + 3] Cycloadditions between Vinylcarbenoids and Dienes: Application to the Total Synthesis of the Natural Product (−)-5-epi-Vibsanin E

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Rh2(R-p-Ph-TPCP)4

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Rh2(S-PTAD)4

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Asymmetric synthesis of tropanes by rhodium-catalyzed [4 + 3] cycloaddition.
Ravisekhara P Reddy et al.
Journal of the American Chemical Society, 129(34), 10312-10313 (2007-08-10)
Kellan N Lamb et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 23(49), 11843-11855 (2017-05-26)
Metal carbenes appended with two electron-donating groups, known as "donor/donor" carbenes, undergo diastereo- and enantioselective rhodium-catalyzed C-H insertion reactions with ether substrates to form benzodihydrofurans. Unlike the reactions of metal carbenes with electron-withdrawing groups attached, the attenuated electrophilicity enables these
Gabrielle S Fleming et al.
Organic letters, 19(19), 5268-5271 (2017-09-12)
The first example of a regioselective and enantioselective intermolecular Buchner ring expansion is reported using continuous flow. The practicality and scope of the reaction are greatly improved under flow conditions. Reactions of ethyl diazoacetate with symmetric and nonsymmetric arenes afford
T Aaron Bedell et al.
Angewandte Chemie (International ed. in English), 55(29), 8270-8274 (2016-05-21)
Methods for functionalizing carbon-hydrogen bonds are featured in a new synthesis of the tricyclic core architecture that characterizes the indoxamycin family of secondary metabolites. A unique collaboration between three laboratories has engendered a design for synthesis featuring two sequential C-H
Ping Lu et al.
The Journal of organic chemistry, 80(15), 7581-7589 (2015-07-07)
A stereodivergent approach to the central thiolane subunit of Nuphar sesquiterpene thioalkaloids has been developed. This approach features a rhodium-catalyzed Stevens-type rearrangement in conjunction with an enzyme resolution reaction. Further elaboration into a polycyclic ring system via alcohol oxidation and
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