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Diastereoselective synthesis of α-amino-β-hydroxyacids

✍ Scribed by Giuseppe Guanti; Luca Banfi; Enrica Narisano; Carlo Scolastico

Publisher
Elsevier Science
Year
1984
Tongue
French
Weight
195 KB
Volume
25
Category
Article
ISSN
0040-4039

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✦ Synopsis

threo-a-Dibensylamino-B-hydroxyesters (2) have been synthesised with high diastereoselectivity through the NaBH reduction of a-dibenzylamino-B-oxoesters (4) and then tranformed into threo-a-amino-B-hydroxyac?ds.

a-Amino-B-hydroxyacids are derivatives of primary importance both as enzymatic inhibitors,* and as starting material for B-lactam antibiotics synthesis.

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Enantiospecific and diastereoselective s
Enantiospecific and diastereoselective synthesis of anti α-hydrazino- and α-amino-β-hydroxyacids through “electrophilic amination” of β-hydroxyesters
✍ Giuseppe Guanti; Luca Banfi; Enrica Narisano 📂 Article 📅 1988 🏛 Elsevier Science 🌐 French ⚖ 827 KB

usA28lWMFxi~ Summary: B-Hydroxyesters 1 a-d weft transformed into corresponding dianions and condensed with di-f-bulylazodicarboxylate to give anfi protected ahydrazino-o-hydroxye31ers 2a-d wilh good diaslereoselecfivities (up lo 94:6). Cleavage of protecting groups followed by ester hydrotysis gave