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905356

Sigma-Aldrich

Rh2(R-PTAD)4

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C80H80N4O16Rh2
Numéro CAS:
909393-65-3
Poids moléculaire :
1559.32
Code UNSPSC :
12161600
Nomenclature NACRES :
NA.22

Forme

powder or crystals

Pf

>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

Clé InChI

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.

Autres remarques

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

Produit(s) apparenté(s)

Réf. du produit
Description
Tarif

905291

Rh2(R-BTPCP)4

905313

Rh2(S-TCPTAD)4

905321

Rh2(R-TCPTAD)4

905348

Rh2(R-p-Ph-TPCP)4

905259

Rh2(S-PTAD)4

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Lot/Batch Number

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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.
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
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
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
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
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