Asymmetric Synthesis of anti-α,β-Disubstituted β-Amino Acid Derivatives by Reaction of N-Alkoxycarbonyl-1-methoxyamines with Optically Active 2-Oxazolidinones

Naoki Kise; Nasuo Ueda

doi:10.1021/ol991053s

October 21, 1999Organic Letters

Asymmetric Synthesis of anti-α,β-Disubstituted β-Amino Acid Derivatives by Reaction of N-Alkoxycarbonyl-1-methoxyamines with Optically Active 2-Oxazolidinones

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Key Points

To develop an asymmetric synthetic method for preparing anti-α,β-disubstituted β-amino acid derivatives using N-alkoxycarbonyl-1-methoxyamines and optically active 2-oxazolidinones.
Reacted N-alkoxycarbonyl-1-methoxyamines with the chiral auxiliary (4S)-3-butyryl-4-isopropyl-2-oxazolidinone.
Converted the resulting adducts into α,β-disubstituted β-amino acid methyl esters and targeted carbapenem precursors.
Coupling yielded intermediate adducts with anti selectivity at 60% diastereomeric excess (de).
Both anti- and syn-α,β-disubstituted β-amino acid methyl esters were produced with 98% enantiomeric excess (ee).
Successfully synthesized an enantiomerically pure precursor for the carbapenem antibiotic PS-5.

Implication

Chemical synthesis study demonstrates stereoselective preparation of disubstituted beta-amino acids using chiral oxazolidinones, indicating viable routes to carbapenem antibiotic precursors.

Abstract

The reaction of N -alkoxycarbonyl-1-methoxyamines and (4 S )-3-butyryl-4-isopropyl-2-oxazolidinone afforded the corresponding adducts with anti selectively (60% de). Both anti - and syn -α,β-disubstituted β-amino acid methyl esters were obtained in 98% ee from the adducts. The enantiomerically pure precursor for the synthesis of carbapenem antibiotic PS-5 was prepared by this method.

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Kise et al. (1999) studied this question.

synapsesocial.com/papers/6a93e03ed3a1effb396d0b27 https://doi.org/10.1021/ol991053s

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Asymmetric Synthesis of anti-α,β-Disubstituted β-Amino Acid Derivatives by Reaction of N-Alkoxycarbonyl-1-methoxyamines with Optically Active 2-Oxazolidinones

Key Points

Implication

Abstract

Discussion

Cite This Study

Asymmetric Synthesis of anti-α,β-Disubstituted β-Amino Acid Derivatives by Reaction of N-Alkoxycarbonyl-1-methoxyamines with Optically Active 2-Oxazolidinones

Key Points

Implication

Abstract

Discussion

Cite This Study

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