| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1347549 | Tetrahedron: Asymmetry | 2008 | 4 Pages |
An efficient asymmetric synthesis of the 2-hydroxymethyl 3,6-disubstituted piperidine alkaloid, (−)-deoxoprosophylline, is described. The key step of this route is the SmI2-mediated cross-coupling of chiral N-tert-butanesulfinyl imine 9 with aldehyde 11 to construct hydroxymethyl-β-amino alcohol 12b in 83% yield and high diastereoselectivity (>99%, de).
Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide
(4R,5S)-Methyl 6-(benzyloxy)-4-hydroxy-5-(2-methylpropane-2-ylsulfinamido)-hexanoateC18H29NO5S[α]D25=-25.5 (c 1.33, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (Rs,4R,5S)
(5R,6S)-6-(Benzyloxymethyl)-5-hydroxypiperidin-2-oneC13H17NO3[α]D25=-18.5 (c 0.14, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (5R,6S)
(5R,6S)-6-(Benzyloxymethyl)-5-(tert-butyldimethylsilyloxy)piperidin-2-oneC19H31NO3Si[α]D25=-39.7 (c 0.6, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (5R,6S)
(2S,3R)-tert-Butyl 2-(benzyloxymethyl)-3-(tert-butyldimethylsilyloxy)-6-oxopiperidine-1-carboxylateC24H39NO5Si[α]D25=+25.2 (c 0.97, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (2R,3S)
tert-Butyl (2S,3R)-1-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-6-oxooctadecan-2-ylcarbamateC36H65NO5Si[α]D25=+11.0 (c 1.64, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (2R,3S)
(R)-N-((2S,3R)-1-(Benzyloxy)-3-hydroxy-6-oxooctadecan-2-yl)-2-methylpropane-2-sulfinamideC29H51NO4S[α]D25=-13.0 (c 0.64, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (Rs,2R,3S)
