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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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250 MG
$432.00

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

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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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Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Ravisekhara P Reddy et al.
Organic letters, 8(16), 3437-3440 (2006-07-28)
[reaction: see text] The dirhodium tetracarboxylate, Rh2(S-PTAD)4, derived from adamantylglycine, is a very effective chiral catalyst for carbenoid reactions. High asymmetric induction was obtained in Rh2(S-PTAD)4-catalyzed intramolecular C-H insertion (94% ee), intermolecular cyclopropanation (99% ee), and intermolecular C-H insertion (92%
Brett D Schwartz et al.
Journal of the American Chemical Society, 131(23), 8329-8332 (2009-05-19)
The total synthesis of (-)-5-epi-vibsanin E (2) has been achieved in 18 steps. The synthesis combines the rhodium-catalyzed [4 + 3] cycloaddition between a vinylcarbenoid and a diene to rapidly generate the tricyclic core with an effective end game strategy
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
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)
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