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(R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine

97%

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Synonym(s):
(R)-Ugi′s amine, (R)-(+)-[1-(Dimethylamino)ethyl]ferrocene
Empirical Formula (Hill Notation):
C14H19FeN
CAS Number:
Molecular Weight:
257.15
MDL number:
PubChem Substance ID:
NACRES:
NA.22

assay

97%

form

liquid

optical activity

[α]20/D +13°, c = 1 in ethanol (5 h)

refractive index

n20/D 1.589 (lit.)

bp

120-121 °C/0.7 mmHg (lit.)

density

1.222 g/mL at 20 °C (lit.)

SMILES string

[Fe].[CH]1[CH][CH][CH][CH]1.C[C@H]([C]2[CH][CH][CH][CH]2)N(C)C

InChI

1S/C9H14N.C5H5.Fe/c1-8(10(2)3)9-6-4-5-7-9;1-2-4-5-3-1;/h4-8H,1-3H3;1-5H;/t8-;;/m1../s1

InChI key

ISOLNZQTVMCEOI-YCBDHFTFSA-N

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Application

(R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine may be used as a starting material to synthesize:
  • chiral 1,2-disubstituted ferrocenyl amino alcohols
  • ferrocene-based P-chiral phosphine ligands
  • optically active α-ferrocenyl tertiary amines
Ligand used in the preparation of chiral allylic alcohols, axially chiral allenecarboxylic esters, and rhodium(I)-catalyzed asymmetric hydrosilylation of ketones.

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Stereoselective synthesis. VIII. Absolute configuration of a 1, 2-disubstituted ferrocene derivative with planar and central elements of chirality and the mechanism of the optically active. alpha.-ferrocenyl tertiary amines.
Battelle LF, et al.
Journal of the American Chemical Society, 95(2), 482-486 (1973)
Chiral auxiliaries for asymmetric synthesis: enantioselective addition of dialkylzincs to aldehydes catalyzed by chiral 1, 2-disubstituted ferrocenyl amino alcohols.
Watanabe M, et al.
The Journal of Organic Chemistry, 56(6), 2218-2224 (1991)
Chiba, T. et al.
Tetrahedron Letters, 36, 1519-1519 (1995)
Nishibayashi, Y.et al.
Journal of the Chemical Society. Chemical Communications, 1375-1375 (1994)
A very simple, highly stereoselective and modular synthesis of ferrocene-based P-chiral phosphine ligands.
Chen W, et al.
Journal of the American Chemical Society, 128(12), 3922-3923 (2006)

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