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Asymmetric synthesis of a branched-chain analogue of azapyranoses from a 5-allylic derivative of 5-nitro-1,3-dioxane. Synthesis of (3R,4S)-6,6-bis(hydroxymethyl)-3,4-dihydroxypiperidin-2-one

✍ Scribed by Anna Budzińska; Wojciech Sas

Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
86 KB
Volume
42
Category
Article
ISSN
0040-4039

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✦ Synopsis

Methyl 4-(5-nitro-1,3-dioxaspiro[5.5]

undecan-5-yl)but-2-enoate 2, obtained from the palladium(0)-catalyzed reaction of a salt of 5-nitro-1,3-dioxane 1 with methyl g-bromocrotonate, was converted into the title piperidinone (ee 78%) in three steps.

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