693626
S-N-(3,5-Di-tert-butylphenyl)-3-methyl-2-(N-formyl-N-methylamino)butanamide
96%
Synonym(s):
Sigamide
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About This Item
Empirical Formula (Hill Notation):
C21H34N2O2
CAS Number:
Molecular Weight:
346.51
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352002
MDL number:
InChI
1S/C21H34N2O2/c1-14(2)18(23(9)13-24)19(25)22-17-11-15(20(3,4)5)10-16(12-17)21(6,7)8/h10-14,18H,1-9H3,(H,22,25)/t18-/m0/s1
SMILES string
CC(C)[C@H](N(C)C=O)C(=O)Nc1cc(cc(c1)C(C)(C)C)C(C)(C)C
InChI key
OVKNTNIBDGTNQY-SFHVURJKSA-N
assay
96%
form
solid
optical activity
[α]22/D -170°, c = 1 in chloroform
mp
180-186 °C
functional group
amide
storage temp.
2-8°C
Application
Used in the synthesis of chiral 1,2-diarylsubstituted aziridines.
signalword
Warning
hcodes
pcodes
Hazard Classifications
Eye Irrit. 2
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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Andrei V Malkov et al.
The Journal of organic chemistry, 72(4), 1315-1325 (2007-02-10)
Asymmetric reduction of ketimines 1 with trichlorosilane can be catalyzed by N-methylvaline-derived Lewis-basic formamides 3a-d with high enantioselectivity (< or =95% ee) and low catalyst loading (1-5 mol %) at room temperature in toluene. Appending a fluorous tag, as in
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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