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Chemoselective Carbonyl Allylations with Alkoxyallylsiletanes.


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.

SUBMITTER: Spaltenstein P 

PROVIDER: S-EPMC6767911 | biostudies-literature | 2019 Apr

REPOSITORIES: biostudies-literature

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Chemoselective Carbonyl Allylations with Alkoxyallylsiletanes.

Spaltenstein Paul P   Cummins Elizabeth J EJ   Yokuda Kelly-Marie KM   Kowalczyk Tim T   Clark Timothy B TB   O'Neil Gregory W GW  

The Journal of organic chemistry 20190313 7


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.  ...[more]

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