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RESEARCH PRODUCT

Chlorodicyclohexylborane-mediated aldol additions of alpha,alpha'-dioxygenated ketones.

Juan MurgaJ. Alberto MarcoMiguel CardaE. FalomirAnd Florenci González

subject

Steric effectsTertiary amineChemistryStereochemistryOrganic ChemistryKeto–enol tautomerismBiochemistryChlorideAldol reactionmedicineChelationStereoselectivityPhysical and Theoretical ChemistryProtecting groupmedicine.drug

description

Boron aldol additions of variously O-protected alpha,alpha'-dioxygenated ketones using dicyclohexylboron chloride and a tertiary amine have been investigated. The stereoselectivity of the process was dependent on the protecting group on the alpha-oxygen atoms. Notably, ketones with bulky silyloxy groups gave syn aldols, most likely via Z enolates. This rules out the participation of chelates during the enolization process, at least in the presence of such sterically crowded protecting groups. An alternative explanation is offered.

yearjournalcountryeditionlanguage
2001-03-27Organic letters
10.1021/ol015542fhttps://pubmed.ncbi.nlm.nih.gov/11263911