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905356

Rh2(R-PTAD)4

powder or crystals

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
MDL number:
MFCD09839139
UNSPSC Code:
12161600
NACRES:
NA.22
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Product Name

Rh2(R-PTAD)4 ,

form

powder or crystals

mp

>300 °C

SMILES string

[Rh]([Rh](OC(=O)[C@H](N%19C(=O)c%20c(cccc%20)C%19=O)C%17%16C[C@@H]%18C[C@@H](C[C@@H](C%18)C%17)C%16)OC(=O)[C@H](N%14C(=O)c%15c(cccc%15)C%14=O)C%12%11C[C@@H]%13C[C@@H](C[C@@H](C%13)C%12)C%11)(OC(=O)[C@H](N9C(=O)c%10c(cccc%10)C9=O)C76C[C@@H]8C[C@@H](C[C@@H]

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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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%
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
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
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