The 1,4-addition of organometallic reagents to enoates derived from pinanediol
✍ Scribed by Sergio Pinheiro; Sérgio F. Pedraza; Mônica A. Peralta; Rafael C. Teixeira; Florence M.C. de Farias; Vı́tor F. Ferreira; Paulo R.R. Costa
- Book ID
- 104359516
- Publisher
- Elsevier Science
- Year
- 2002
- Tongue
- English
- Weight
- 199 KB
- Volume
- 13
- Category
- Article
- ISSN
- 0957-4166
No coin nor oath required. For personal study only.
✦ Synopsis
The complex-induced, proximity effect-promoted 1,4-addition of RCu•BF 3 and R 2 CuLi to enoates derived from (-)-pinanediol leads to adducts with the opposite sense of chirality (up to 98% d.e.).
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Piperidinones with a 2-bromobenzyl substituent in the 5-position were subjected to a Heck coupling reaction with ethyl acrylate resulting in the highly functionalized cinnamates 9a-d. A subsequent deprotonation of the piperidinones using NaN(SiM 3 ) 2 in THF induced an intramolecular Michael additio