Chemoselective Carbonyl Allylations with Alkoxyallylsiletanes.
J Org Chem
; 84(7): 4421-4428, 2019 04 05.
Article
em En
| MEDLINE
| ID: mdl-30811929
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.
Texto completo:
1
Bases de dados:
MEDLINE
Assunto principal:
Silanos
/
Compostos Alílicos
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2019
Tipo de documento:
Article
País de afiliação:
Estados Unidos