Skip to Content
Merck
All Photos(3)

Documents

905259

Sigma-Aldrich

Rh2(S-PTAD)4

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(3)

About This Item

Empirical Formula (Hill Notation):
C80H80N4O16Rh2
CAS Number:
909389-99-7
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?;;/m1111../s1

InChI key

SGEDWOHAUXKUGM-PAPHCAFZSA-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 stereocontrol.

Other Notes

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

Dirhodium Tetracarboxylates Derived from Adamantylglycine as Chiral Catalysts for Enantioselective C-H Aminations

Enantioselective Synthesis of Trifluoromethyl-?Substituted Cyclopropanes

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Justin R Denton et al.
Chemical communications (Cambridge, England), (10), 1238-1240 (2008-03-01)
Nitrile-substituted cyclopropanes are readily synthesized in a stereocontrolled fashion from the intermolecular cyclopropanation between 2-diazo-2-phenylacetonitrile and electron-rich olefins, catalyzed by the chiral dirhodium complex, Rh(2)(S-PTAD)(4).
Chen Kong et al.
Journal of the American Chemical Society (2016-10-05)
A mechanism study to identify the elements that control the chemoselectivity of metal-catalyzed N-atom transfer reactions of styryl azides is presented. Our studies show that the proclivity of the metal N-aryl nitrene to participate in sp3-C-H bond amination or electrocyclization
Justin R Denton et al.
Organic letters, 11(4), 787-790 (2009-01-17)
The reaction of a variety of alpha-aryl-alpha-diazo ketones with activated olefins, catalyzed by the adamantyl glycine-derived dirhodium complex Rh(2)(S-PTAD)(4), generates cyclopropyl ketones with high diastereoselectivity (up to >95:5 dr) and enantioselectivity (up to 98% ee). Intermolecular C-H functionalization of 1,4-cyclohexadiene
Romain J Lepage et al.
Chemical communications (Cambridge, England), 53(30), 4219-4221 (2017-03-31)
Acyclic methylene acetals bearing two diazoester subunits have been converted to [5,5]-spiroacetals via bidirectional C-H insertion under Rh(ii) catalysis. Using a chiral Rh(ii) catalyst, the major diastereomer can be produced in high enantiomeric excess (89%).
Yan Su et al.
Organic letters, 18(17), 4356-4359 (2016-08-17)
Optically active cis-cyclopropane carboxylates are prepared via the Rh2(S-PTAD)4-catalyzed cyclopropanation of α-silyl styrenes with aryl diazoacetates followed by desilylation of the resulting silyl cyclopropane carboxylates. The conjugation of the aryl ring with C═C bond and π stacking are proposed for
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service