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Total synthesis of (+) monomorine I from chiral cyclic β-enamino ester

✍ Scribed by C. Saliou; A. Fleurant; J.P. Célérier; G. Lhommet

Publisher
Elsevier Science
Year
1991
Tongue
French
Weight
196 KB
Volume
32
Category
Article
ISSN
0040-4039

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✦ Synopsis

We &scribe the total synthesis of (+) Monomorine I 1 and the preparation of cis-2,5-disubstituted functionalized pyrrolidines via cyclic p-enamino esters 4, starting from (S)-pyroglutamic acid.

📜 SIMILAR VOLUMES

Chiral cyclic β-amino esters. Part II: S
Chiral cyclic β-amino esters. Part II: Synthesis by diastereoselective reduction of enamino esters
✍ J. Blot; A. Bardou; C. Bellec; M.-C. Fargeau-Bellassoued; J.P. Célérier; G. Lhom 📂 Article 📅 1997 🏛 Elsevier Science 🌐 French ⚖ 182 KB

Catalytic and chemical reductions of chiral pyrrolidine 13-enamino esters provides corresponding [3-amino esters with good to moderate diastereomer excesses. The unexpected major diastereomer 5 comes from a reduction process which amounts to an anti hydrogen addition.