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Efficient synthesis of (2R,3S)- and (2S,3S)-2-amino-1,3,4-butanetriols through stereodivergent hydroxymethylation of d-glyceraldehyde nitrones

✍ Scribed by Pedro Merino; Santiago Franco; Francisco L. Merchan; Julia Revuelta; Tomas Tejero

Publisher: Elsevier Science
Year: 2002
Tongue: French
Weight: 65 KB
Volume: 43
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)02191-8

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✦ Synopsis

The nucleophilic addition of two alkoxymethyllithium derivatives to three D-glyceraldehyde derived nitrones has been investigated. The diastereofacial selectivity of the reaction could be controlled by the appropriate use of Lewis acids as precomplexing agents of the nitrones. The obtained syn and anti adducts were further converted into C-4 building blocks and b-hydroxy-a-aminoacids.

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