Chiral cyclic β-amino esters. Part I: Synthesis by diastereospecific alkylation
✍ Scribed by A. Bardou; J.P. Célérier; G. Lhommet
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 138 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0040-4039
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📜 SIMILAR VOLUMES
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.
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.
A short and convenient asymmetric synthesis of cl-alkyl a-amino acids is described, using (S)(-)-I-dimethoxymethyl-Z-methoxymethyl pyrrolidine (5) as chiral auxiliary reagent.