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Organocatalytic asymmetric synthesis of quinine and quinidine

✍ Scribed by Shaheen M. Sarkar; Yuko Taira; Ayako Nakano; Keisuske Takahashi; Jun Ishihara; Susumi Hatakeyama

Book ID
104098767
Publisher
Elsevier Science
Year
2011
Tongue
French
Weight
513 KB
Volume
52
Category
Article
ISSN
0040-4039

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✦ Synopsis

Quinine and quinidine were synthesized by a highly enantio-and stereoselective approach starting from a proline-catalyzed asymmetric cycloaldolization of benzyl bis(2-formylethyl)carbamate which gave a 70:30 mixture of (3R,4R)-N-Cbz-3-hydroxymethyl-4-hydroxypiperidine (96% ee) and its 4S-epimer (92% ee) in 94% yield after in situ NaBH 4 reduction.

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## Abstract Die stereoselektive Synthese der beiden Cinchona‐Nebenalkaloide 9‐__epi__Chinin (**14**) und 9‐__epi__‐Chinidin (**15**) wird beschrieben.