| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1347834 | Tetrahedron: Asymmetry | 2007 | 5 Pages |
An efficient enantioselective synthesis leading directly to (+)-(S)-dapoxetine has been described for the first time using a Sharpless asymmetric dihydroxylation, Barton–McCombie deoxygention, and Mitsunobu reaction as the key steps.
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(S)-N,N-Dimethyl-3-(naphthalen-1-yloxy)-1-phenylpropan-1-amineC21H23NO[α]D25=+64.2 (c 0.3, CHCl3)Source of chirality: Sharpless asymmetric dihydroxylationAbsolute configuration: (S)
(S)-3-(N,N-Dimethylamino)-3-phenylpropan-1-olC11H17NO[α]D25=+39.2 (c 0.6, CHCl3)Source of chirality: Sharpless asymmetric dihydroxylationAbsolute configuration: (S)
tert-Butyl (S)-2-(methoxycarbonyl)-1-phenylethylcarbamateC15H21NO4[α]D25=-31.5 (c 1.31, CH3COCH3)Source of chirality: Sharpless asymmetric dihydroxylationAbsolute configuration: (S)
(2R,3S)-Methyl 2,3-dihydroxy-3-phenylpropanoate 5C10H12O4[α]D25=+3.5 (c 1.19, EtOH)Source of chirality: Sharpless asymmetric dihydroxylationAbsolute configuration: (2R,3S)
Methyl (4R,5S)-5-phenyl-1,3,2-dioxathiolane-4-carboxylate S-oxideC10H10O5S[α]D25=-92.3 (c 1.1, CH2Cl2)Source of chirality: Sharpless asymmetric dihydroxylationAbsolute configuration: (2R,3S)
Methyl (2R,3R)-3-azido-2-hydroxy-3-phenylpropanoateC10H11N3O3[α]D25=-60.0 (c 4.44, EtOH)Source of chirality: Sharpless asymmetric dihydroxylationAbsolute configuration: (2R,3S)
tert-Butyl (1R,2R)-2-(methoxycarbonyl)-2-hydroxy-1-phenylethylcarbamateC15H21NO5[α]D25=-78.4 (c 1.91, CH3COCH3)Source of chirality: Sharpless asymmetric dihydroxylationAbsolute configuration: (1R,2R)
tert-Butyl (1R,2R)-2-(methoxycarbonyl)-2-O-(S-methyldithiocarbonate)-1-phenylethylcarbamateC17H23NO5S2[α]D25=-47.3 (c 1.13, CH3COCH3)Source of chirality: Sharpless asymmetric dihydroxylationAbsolute configuration: (1R,2R)
tert-Butyl (S)-3-hydroxy-1-phenylpropylcarbamateC14H21NO3[α]D25=-53.0 (c 1.27, CH3COCH3)Source of chirality: Sharpless asymmetric dihydroxylationAbsolute configuration: (S)
