Abstract
Treatment of a range of cis-and trans-2-ferrocenyl-3-pivaloyl-4-alkyl-1,3-oxazolidin-5-ones with LDA followed by the addition of allyl bromide promotes highly stereoselective allylation (>98% de) at the 4-position of the oxazolidinone ring anti to the stereodirecting 2-ferrocenyl group. Hydrolysis of the resultant 4,4-disubstituted oxazolidinones (>98% de) yields enantiomeric (R)- and (S)-2-alkyl-2-aminopent-4-enoic acids in high ee. Furthermore, the aldol reaction of the lithium enolate of cis-2-ferrocenyl-3-pivaloyl-4-methyl-1,3-oxazolidin-5-one with benzaldehyde followed by in situ O-protection affords O-protected aldol products in >98% de, with hydrolysis affording (2R,3S)-2-amino-2-methyl-3-hydroxy-3-phenylpropanoic acid in >98% de.
Original language | English |
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Pages (from-to) | 527-536 |
Number of pages | 10 |
Journal | Organic & Biomolecular Chemistry |
Volume | 7 |
Issue number | 3 |
DOIs | |
Publication status | Published - 2009 |
Keywords
- ALPHA-AMINO-ACIDS
- METHYL-BETA-PHENYLSERINE
- ENANTIOSELECTIVE SYNTHESIS
- ENANTIOMERICALLY PURE
- MICROBIAL METABOLITE
- NEUROBLASTOMA-CELLS
- CHIRAL AUXILIARY
- PROTEIN DESIGN
- IMINO ESTERS
- DERIVATIVES