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905259

Sigma-Aldrich

Rh2(S-PTAD)4

Synonym(s):

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

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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

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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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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
Zhanjie Li et al.
Journal of the American Chemical Society, 132(1), 396-401 (2009-12-10)
The rhodium-catalyzed reaction of racemic allyl alcohols with methyl phenyldiazoacetate or methyl styryldiazoacetate results in a two-step process, an initial oxonium ylide formation followed by a [2,3]-sigmatropic rearrangement. This process competes favorably with the more conventional O-H insertion chemistry as
Kuangbiao Liao et al.
Nature, 533(7602), 230-234 (2016-05-14)
The laboratory synthesis of complex organic molecules relies heavily on the introduction and manipulation of functional groups, such as carbon-oxygen or carbon-halogen bonds; carbon-hydrogen bonds are far less reactive and harder to functionalize selectively. The idea of C-H functionalization, in
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
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%).
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