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Azetidin-3-ones from (S)-α-Amino Acids and Their Reactions with Nucleophiles: Preparation of some azetidine-containing amino-alcohol and amino-acid derivatives

✍ Scribed by Joachim Podlech; Dieter Seebach

Publisher: John Wiley and Sons
Year: 1995
Tongue: German
Weight: 673 KB
Volume: 78
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19950780516

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✦ Synopsis

Abstract

The reactions of azetidin‐3‐ones 6–10, readily available from the amino acids L‐alanine, L‐phenylalanine, L‐valine, L‐lysine, and L‐aspartic acid, via the corresponding diazo ketones, with nucleophilic reagents such as complex hydrides, Grignard compounds, an ester enolate, and a Wittig ylide give the expected products 11–19 in good yields and mostly in high diastereoselectivities. New amino‐alcohol, γ‐amino‐ and γ‐amino‐β‐hydroxy‐carboxylic‐acid derivatives of known configurations are thus available.

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