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Aza-claisen rearrangement of amide enolates. Stereoselective synthesis of 2,3-disubstituted carboxamides

✍ Scribed by Tetsuto Tsunoda; Osamu Sasaki; Shô Itô

Publisher
Elsevier Science
Year
1990
Tongue
French
Weight
236 KB
Volume
31
Category
Article
ISSN
0040-4039

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✦ Synopsis

Aza-Claisen rearrangement of enolates of N-2-butenyl-N-butylpropanamides proceeded with high stereoselectivity (up to 99.5:0.5) to yield N-butyl-2,3-dimethyl-4-pentenamides (up to 94% yield).

Claisen rearrangement of ester enolates initiated by Irelanda) has substantial synthetic value and widespread application in the homologation of alcohols.3)

From the present standard, however, the diastereoselectivity

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Asymmetric aza-Claisen rearrangement: Sy
Asymmetric aza-Claisen rearrangement: Synthesis of (+)-dihydropallescensin-2 [(+)-penlanpallescensin].
✍ Mark J. Kurth; Christopher J. Soares 📂 Article 📅 1987 🏛 Elsevier Science 🌐 French ⚖ 260 KB

## Synthetic confirmation of the C(l ')-(S)-configuration of (+)-dihydropallescensin-2 (1) is reporled, the key reaction being a &iron-medialed asymmetric aza-Claisen rearrangement (6-7). In 1982, Faulkner et.al.la reported the isolation of dihydropallescensin-2 from the nudibranch Cadlina luteom