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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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Rh2(R-p-Ph-TPCP)4

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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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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
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%
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
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