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Condensation reactions of α-amino-zincenamines with aldehydes; Application to indolizines

✍ Scribed by Elmo Wissing; Remco W.A. Havenith; Jaap Boersma; Gerard van Koten

Book ID
104214792
Publisher
Elsevier Science
Year
1992
Tongue
French
Weight
236 KB
Volume
33
Category
Article
ISSN
0040-4039

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✦ Synopsis

The zinc-enamine 1 is easily accessible via the reaction of Et$n with t-BuN=CHCH=Nt-Bu and is reactive rowarak aldehydes. The condensation reaction of 1 with 2-pyridine-carboxaldehyde results in

the &mnally instable zinc-aldolare 2 b that subsequently rearranges to the indolizine 4.

📜 SIMILAR VOLUMES

Double stereodifferentiating crotylation
Double stereodifferentiating crotylation reactions with α-amino aldehydes: Asymmetric synthesis of vicinal amino alcohol synthons
✍ James S. Panek; Ping Liu 📂 Article 📅 1997 🏛 Elsevier Science 🌐 French ⚖ 212 KB

The sense and level of 1,2-asymmetric induction have been evaluated in the BF3.OEI ~ promoted addition of (E)crotylsilanes (R)-I and (S)-I to or-amino aldehydes 2a through 2d. The sense of carbonyl diastereoface selectivity was shown to be dependent of the chirality of the silane reagent.