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Enantiospecific and diastereoselective synthesis of anti α-hydrazino- and α-amino-β-hydroxyacids through “electrophilic amination” of β-hydroxyesters

✍ Scribed by Giuseppe Guanti; Luca Banfi; Enrica Narisano

Publisher
Elsevier Science
Year
1988
Tongue
French
Weight
827 KB
Volume
44
Category
Article
ISSN
0040-4020

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✦ Synopsis

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 the previously unknown anli a-hydrazino-P-hydroxyacids 4a-d, which were in turn converted by hydrogenolysis inlo anti a-amino-P-hydroxyacids Sa-d. Starting from (S)

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