| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1348897 | Tetrahedron: Asymmetry | 2006 | 5 Pages |
TMSCN asymmetrically adds to a variety of ketones by catalysis with 1/Ph3PO. This is a double activation where 1 acts as a Lewis acid and Ph3PO as a Lewis base. Various ketones were subjected to the enantioselective addition to give up to 85% ee.
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(R)-2-Phenyl-2-(trimethylsilyloxy)propanenitrileC12H17NOSiEe = 63%[α]D24=+10.4 (c 1.14, CHCl3)
(R)-2-(3-Chlorophenyl)-2-(trimethylsilyloxy)propanenitrileC12H16ClNOSiEe = 63%[α]D24=+11.2 (c 1.3, CHCl3)
C12H16ClNOSi(R)-2-(4-Chlorophenyl)-2-(trimethylsilyloxy)propanenitrileEe = 57%[α]D24=+12.4 (c 1.68, CHCl3)
C12H16BrNOSi(R)-2-(4-Bromophenyl)-2-(trimethylsilyloxy)propanenitrileEe = 85%[α]D24=+20.7 (c 1.65 CHCl3)
(R)-2-(4-Fluorophenyl)-2-(trimethylsilyloxy)propanenitrileC12H16FNOSiEe = 60%[α]D24=+15.3 (c 1.4 CHCl3)
(R)-2-(4-Nitrophenyl)-2-(trimethylsilyloxy)propanenitrileC12H16N2O3SiEe = 50%[α]D22=+8.1 (c 1.62 CHCl3)
(R)-2-(4-Methoxyphenyl)-2-(trimethylsilyloxy)propanenitrileC13H19NO2SiEe = 82%[α]D20=+18.2 (c 1.5 CHCl3)
(R)-3-Methyl-2-phenyl-2-(trimethylsilyloxy)butanenitrileC14H21NOSiEe = 57%[α]D20=+23.1 (c 2.1 CHCl3)
(R)-2-Methyl-4-phenyl-2-(trimethylsilyloxy)butanenitrileC14H21NOSiEe = 60%[α]D20=+9.2 (c 1.8 CHCl3)
(R)-1-(Trimethylsilyloxy)-2,3-dihydro-1H-indene-1-carbonitrileC13H17NOSiEe = 58%[α]D23=+14.4 (c 1.4 CHCl3)
