| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1350866 | Tetrahedron: Asymmetry | 2005 | 4 Pages |
We report herein, the novel enzymatic desymmetrization of 2-tert-butoxycarbonylamino-2-methyl-1,3-propanediol 1. This method makes it possible to prepare (S)-N-Boc-N,O-isopropylidene-α-methylserinal 3, which is a chiral building block for the synthesis of a variety of α-substituted alanine derivatives. Moreover, optically active (4R)-methyl-4-[2-(thiophen-2-yl)ethyl]oxazolidin-2-one 4, one of the key intermediates in the synthesis of a novel immunosuppressant, has been prepared by this methodology.
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(4R)-Methyl-4-[2-(thiophen-2-yl)ethyl]oxazolidin-2-oneC10H13NO2SEe = >99%[α]D25=+7.8 (c 2, CHCl3)Source of chirality: enzymatic desymmetrizationAbsolute configuration: 4R
![Enzymatic desymmetrization of 2-amino-2-methyl-1,3-propanediol: asymmetric synthesis of (S)-N-Boc-N,O-isopropylidene-α-methylserinal and (4R)-methyl-4-[2-(thiophen-2-yl)ethyl]oxazolidin-2-one](/preview/png/1350866.png "First Page Preview: Enzymatic desymmetrization of 2-amino-2-methyl-1,3-propanediol: asymmetric synthesis of (S)-N-Boc-N,O-isopropylidene-α-methylserinal and (4R)-methyl-4-[2-(thiophen-2-yl)ethyl]oxazolidin-2-one")