693561
(S)-N-(3,5-Dimethylphenyl)-3-methyl-2-(N-formyl-N-methylamino)butanamide
97%
Synonym(s):
Kenamide
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About This Item
Empirical Formula (Hill Notation):
C15H22N2O2
CAS Number:
Molecular Weight:
262.35
MDL number:
UNSPSC Code:
12352002
PubChem Substance ID:
NACRES:
NA.22
assay
97%
form
solid
optical activity
[α]22/D -229°, c = 1 in chloroform
mp
97-104 °C
storage temp.
2-8°C
SMILES string
CC(C)[C@H](N(C)C=O)C(=O)Nc1cc(C)cc(C)c1
InChI
1S/C15H22N2O2/c1-10(2)14(17(5)9-18)15(19)16-13-7-11(3)6-12(4)8-13/h6-10,14H,1-5H3,(H,16,19)/t14-/m0/s1
InChI key
WWUZCRRIJZUXEZ-AWEZNQCLSA-N
Application
Used in the asymmetric reduction of prochiral N-aryl ketimines with trichlorosilane.†
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Malkov, A. V.; Stoncius, S.; MacDougall, K. N.; Mariani, A.; McGeoch, G. D.; Kocovsky, P.
Tetrahedron, 62, 264-264 (2006)
Enantioselective synthesis of 1,2-diarylaziridines by the organocatalytic reductive amination of alpha-chloroketones.
Andrei V Malkov et al.
Angewandte Chemie (International ed. in English), 46(20), 3722-3724 (2007-04-07)
Andrei V Malkov et al.
Organic letters, 6(13), 2253-2256 (2004-06-18)
[reaction: see text] Asymmetric reduction of ketimines 1 with trichlorosilane can be catalyzed by a new N-methyl L-valine derived Lewis basic organocatalyst, such as 4d, with high enantioselectivity. The structure-reactivity investigation suggests hydrogen bonding and arene-arene interactions between the catalyst
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