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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
UNSPSC Code:
12161600
NACRES:
NA.22

form

powder or crystals

mp

>300 °C

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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905313

Rh2(S-TCPTAD)4

905321

Rh2(R-TCPTAD)4

905348

Rh2(R-p-Ph-TPCP)4

905259

Rh2(S-PTAD)4

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Cristian Soldi et al.
Journal of the American Chemical Society, 136(43), 15142-15145 (2014-10-14)
The first asymmetric insertion reactions of donor-donor carbenoids, i.e., those with no pendant electron-withdrawing groups, are reported. This process enables the synthesis of densely substituted benzodihydrofurans with high levels of enantio- and diastereoselectivity. Preliminary results show similar efficiency in the
Andrew DeAngelis et al.
Journal of the American Chemical Society, 133(6), 1650-1653 (2011-01-27)
A catalytic, enantioselective method for the C-H functionalization of indoles by diazo compounds has been achieved. With catalytic amounts of Rh(2)(S-NTTL)(4), the putative Rh-carbene intermediates from α-alkyl-α-diazoesters react with indoles at C(3) to provide α-alkyl-α-indolylacetates in high yield and enantioselectivity.
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
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