| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1346559 | Tetrahedron: Asymmetry | 2011 | 4 Pages |
Simple amino acid-derived esters have been identified as promising chiral sources for the ytterbium-catalyzed aldol-Tishchenko reaction of aromatic aldehydes with aliphatic ketones. The 1,3-anti-diols with three stereogenic centers were isolated in excellent yields, complete anti-diastereocontrol and enantioselectivities of up to 50% ee.
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2,4,6-Triisopropylbenzyl (2S)-2-(dimethylamino)propanoateC21H35NO2[α]D25.5=-11.3 (c 0.32, CHCl3)Source of chirality: from starting material, alanineAbsolute configuration: (2S)
2,4,6-Trimethylbenzyl (2S)-2-(dimethylamino)propanoateC15H23NO2[α]D25.6=-14.9 (c 1.08, CHCl3)Source of chirality: from starting material, alanineAbsolute configuration: (2S)
1-Naphthylmethyl (2S)-2-(dimethylamino)propanoateC16H19NO2[α]D25.7=-12.8 (c 1.06, CHCl3)Source of chirality: from starting material, alanineAbsolute configuration: (2S)
Diphenylmethyl (2S)-2-(dimethylamino)propanoateC18H21NO2[α]D25.2=-11.0 (c 1.06, CHCl3)Source of chirality: from starting material, alanineAbsolute configuration: (2S)
Benzyl (2S)-2-(dimethylamino)-3-methylbutanoateC14H21NO2[α]D23.3=-7.6 (c 0.96, CHCl3)Source of chirality: from starting material, valineAbsolute configuration: (2S)
Benzyl (2S)-1-methyltetrahydro-1H-pyrrole-2-carboxylateC13H17NO2[α]D24.5=-71.1 (c 0.28, CHCl3)Source of chirality: from starting material, prolineAbsolute configuration: (2S)
Benzyl (2S)-2-(dimethylamino)propanoateC12H17NO2[α]D25.1=-16.5 (c 0.62, CHCl3)Source of chirality: from starting material, alanineAbsolute configuration: (2S)
4-Methylbenzyl (2S)-2-(dimethylamino)propanoateC13H19NO2[α]D25.9=-21.8 (c 0.40, CHCl3)Source of chirality: from starting material, alanineAbsolute configuration: (2S)
4-Methoxybenzyl (2S)-2-(dimethylamino)propanoateC13H19NO3[α]D25.7=-15.5 (c 0.27, CHCl3)Source of chirality: from starting material, alanineAbsolute configuration: (2S)
4-Fluorobenzyl (2S)-2-(dimethylamino)propanoateC12H16FNO2[α]D25.9=-24.4 (c 0.06, CHCl3)Source of chirality: from starting material, alanineAbsolute configuration: (2S)
