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ChemInform Abstract: Nucleophilic Additions of Grignard Reagents to N-Benzyl-2,3-O-isopropylidene-D-glyceraldehyde Nitrone (BIGN). Synthesis of (2S,3R) and (2S,3S)-3-Phenylisoserine.

✍ Scribed by P. MERINO; E. CASTILLO; S. FRANCO; F. L. MERCHAN; T. TEJERO

Publisher
John Wiley and Sons
Year
2010
Weight
38 KB
Volume
30
Category
Article
ISSN
0931-7597

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✦ Synopsis

Nucleophilic Additions of Grignard Reagents to N-Benzyl-2,3-O-isopropylidene-D-glyceraldehyde Nitrone (BIGN). Synthesis of (2S,3R) and (2S,3S)-3-Phenylisoserine.

-The addition of Grignard reagents to the nitrone (I) proceeds with high anti or syn selectivity depending on the Lewis acid used. The resulting products can easily be transformed into 3-amino-1,2-diols and Ξ±-hydroxy-Ξ²-amino acid derivatives like (X) and (XIV). Ξ±-Hydroxy-Ξ²-amino acids are present in a number of biologically active compounds.

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✍ P. MERINO; E. CASTILLO; S. FRANCO; F. L. MERCHAN; T. TEJERO πŸ“‚ Article πŸ“… 2010 πŸ› John Wiley and Sons βš– 35 KB

Ready Access to Enantiopure 5-Substituted-3-pyrrolin-2-ones from N-Benzyl-2,3-O-isopropylidene-D-glyceraldehyde Nitrone (BIGN). -A short and efficient route to the title compounds is developed. These pyrrolinones are useful synthetic synthons and can be employed for the preparation of highly functi