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Chemoselective Carbonyl Allylations with Alkoxyallylsiletanes.
- Source :
-
The Journal of organic chemistry [J Org Chem] 2019 Apr 05; Vol. 84 (7), pp. 4421-4428. Date of Electronic Publication: 2019 Mar 13. - Publication Year :
- 2019
-
Abstract
- Alkoxyallylsiletanes are capable of highly chemo- and diastereoselective carbonyl allylsilylations. Reactive substrates include salicylaldehydes and glyoxylic acids. Chemoselectivity in these reactions is thought to arise from a mechanism involving first exchange of the alkyoxy group on silicon with a substrate hydroxyl followed by activation of a nearby carbonyl by the Lewis acidic siletane and intramolecular allylation. In this way, substrates containing multiple reactive carbonyl groups (e.g., dialdehyde or triketone) can be selectively monoallylated, even overcoming inherent electrophilicity bias.
Details
- Language :
- English
- ISSN :
- 1520-6904
- Volume :
- 84
- Issue :
- 7
- Database :
- MEDLINE
- Journal :
- The Journal of organic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 30811929
- Full Text :
- https://doi.org/10.1021/acs.joc.8b03028