title: Thiourea/proline derivative-catalyzed synthesis of tetrahydrofuran derivatives: a mechanistic view.
abstract: A thiourea/proline derivative-catalyzed synthesis of linear α-substituted tetrahydrofuran/pyran derivatives starting with lactol substrates is presented. This study demonstrates the utility and potential complications of using (thio)urea/proline cocatalysis as each of these catalysts is necessary to provide the observed reactivity, but a time-dependent decrease in enantioselectivity is observed. New mechanistic insights into (thio)urea/proline cocatalysis are presented.
authors.affiliation: Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853, USA.
authors.forename: Suzanne M
authors.initials: SM
authors.lastname: Opalka
authors.forename: Jeremy L
authors.initials: JL
authors.lastname: Steinbacher
authors.forename: Brandon A
authors.initials: BA
authors.lastname: Lambiris
authors.forename: D Tyler
authors.initials: DT
authors.lastname: McQuade
mesh_terms: D002384:Catalysis; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011392:Proline / Q000737:chemistry*; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013890:Thiourea / Q000031:analogs & derivatives / Q000737:chemistry*
chemical_list: D005663:Furans; D011714:Pyrans; C018674:tetrahydrofuran; D011392:Proline; D013890:Thiourea