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Stereochemical Aspects of a Two-Step Staudinger Reaction − Asymmetric Synthesis of Chiral Azetidine-2-ones

✍ Scribed by Alessandro Bongini; Mauro Panunzio; Giovanni Piersanti; Elisa Bandini; Giorgio Martelli; Giuseppe Spunta; Alessandro Venturini

Publisher
John Wiley and Sons
Year
2000
Tongue
English
Weight
423 KB
Volume
2000
Category
Article
ISSN
1434-193X

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✦ Synopsis

Reaction of N-trialkylsilylimines with a variety of glycine-derived ketenes produced 1,3-azadienes, which in some cases have been isolated and characterised. A conrotatory ring closure of these compounds gave rise to the formation of the azetidine-2-ones, thus allowing a formal two-step Staudinger reaction. Exclusive trans diastereoselectivity was observed. A less stringent diastereofacial selectivity was obtained. A set of experiments has been performed in order to evaluate the influence of the structural parameters as well as reaction [a

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