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Dibutylboron triflate promoted conjugate addition of benzylic and allylic organocopper reagents to chiral α,β-unsaturated N-acyl imidazolidinones

✍ Scribed by Pieter S. van Heerden; Barend C.B. Bezuidenhoudt; Daneel Ferreira

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
192 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis

The organocopper-Lewis acid system, RCu-TMEDA-BuzBOTf, is useful for conjugate addition to highly constrained chiral c~,lS-unsaturated N-acyl imidazolidiannes. In comparison with the corresponding TMSCi-activated reagents, Bu2BOTf exhibits a dramatic increase in reactivity during 1,4-addition of benzylic and allylic organocopper reagents, which react more readily with crotonoyl-, and especially cinnamoyl imides.

📜 SIMILAR VOLUMES

Lewis acid promoted conjugate addition o
Lewis acid promoted conjugate addition of vinylmagnesium bromide to chiral α,β-unsaturated N-acyl oxazolidinones
✍ Yinglin Han; Victor J. Hruby 📂 Article 📅 1997 🏛 Elsevier Science 🌐 French ⚖ 185 KB

Lewis acid promoted conjugated additions of vinylmagnesium bromide to chiral ot,13unsaturated N-acyl oxazolidinones are described. A series of enatiomerically pure [5-branched 4-pentenoic acid derivatives have been synthesized with high diastereoselectivity.