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Enantioselective Synthesis of (2 R ,4 S )- and (2 S ,4 R )-4-Hydroxypipecolic Acid from d -Glucoheptono-1,4-lactone

✍ Scribed by Di Nardo, Christián; Varela, Oscar

Book ID
119978998
Publisher
American Chemical Society
Year
1999
Tongue
English
Weight
151 KB
Volume
64
Category
Article
ISSN
0022-3263

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Asymmetric synthesis of (2S,4R)-4-hydrox
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An asymmetric synthesis of (2S,4R)-4-hydroxypipecolic acid was accomplished in eight steps and 31% overall yield.

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## Abstract A new synthetic route to enantiopure (2__S__,4__R__)‐4‐hydroxypipecolic acid from commercial ethyl (3__S__)‐4‐chloro‐3‐hydroxybutanoate is reported. The synthesis is based on the Pd‐catalyzed methoxycarbonylation of a 4‐alkoxy‐substituted δ‐valerolactam‐derived vinyl triflate followed b

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✍ Mark Sabat; Carl R Johnson 📂 Article 📅 2001 🏛 Elsevier Science 🌐 French ⚖ 104 KB

Syntheses of protected derivatives of both enantiomers of trans-4-hydroxypipecolic acid (2) and the natural product (-)-SS20846A (3) were accomplished from vinylglycinols. Key transformations involved construction of the piperidine ring via ring-closing metathesis (Grubbs' catalyst) and installation