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Chiral heterocyclic β-enamino esters: convenient synthesis and diastereoselective reduction

✍ Scribed by Sandrine Calvet; Olivier David; Corinne Vanucci-Bacqué; Marie-Claude Fargeau-Bellassoued; Gérard Lhommet

Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
205 KB
Volume
59
Category
Article
ISSN
0040-4020

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✦ Synopsis

The preparation of chiral pyrrolidine and piperidine b-enamino esters starting from v-halogeno b-keto esters, their diastereoselective reduction and the subsequent cleavage of the chiral auxiliary are described.

📜 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.