title: Intercepting the Breslow intermediate via Claisen rearrangement: synthesis of complex tertiary alcohols without organometallic reagents.
abstract: A novel Claisen rearrangement in which the Breslow intermediate is engaged as a hydroxy-substituted N,S-ketene acetal to provide complex 3° alcohols without the use of organometallic reagents is reported. The reaction constitutes an unprecedented reactivity mode for the Breslow intermediate.
authors.affiliation: 119 Chemistry Building, University of Arkansas, Fayetteville, Arkansas 72701, USA.
authors.forename: Sefat
authors.initials: S
authors.lastname: Alwarsh
authors.forename: Kolawole
authors.initials: K
authors.lastname: Ayinuola
authors.forename: Silvana S
authors.initials: SS
authors.lastname: Dormi
authors.forename: Matthias C
authors.initials: MC
authors.lastname: McIntosh
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D052160:Benzothiazoles / Q000138:chemical synthesis* / Q000737:chemistry; D005030:Ethylenes / Q000737:chemistry; D007202:Indicators and Reagents; D007659:Ketones / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D052160:Benzothiazoles; D005030:Ethylenes; D007202:Indicators and Reagents; D007659:Ketones; C008223:ketene