title: Use of hindered silyl ethers as protecting groups for the non-aldol aldol process.
abstract: [reaction: see text] Bulky epoxy bis-silyl ethers, e.g., 15, derived from 5-trialkylsilyloxy-2-alken-1-ols by epoxidation and silylation were treated with TMSOTf to afford non-aldol aldol rearrangement products, the 3,5-bis(silyloxy)alkanals, e.g., 16, with little to none of the corresponding tetrahydrofurans.
authors.affiliation: Department of Chemistry and Biochemistry, University of California-Los Angeles, Los Angeles, California 90095-1569, USA. jung@chem.ucla.edu
authors.forename: Michael E
authors.initials: ME
authors.lastname: Jung
authors.forename: Barbara
authors.initials: B
authors.lastname: Hoffmann
authors.forename: Bernhard
authors.initials: B
authors.lastname: Rausch
authors.forename: Jean-Marie
authors.initials: JM
authors.lastname: Contreras
mesh_terms: D000447:Aldehydes / Q000138:chemical synthesis; D004987:Ethers / Q000737:chemistry*; D017646:Organosilicon Compounds / Q000737:chemistry*; D011422:Propionates / Q000138:chemical synthesis*
chemical_list: D000447:Aldehydes; D004987:Ethers; D017646:Organosilicon Compounds; D011422:Propionates