title: Bocdene and mocdene derivatives of catechols and catecholamines.
abstract: [reaction in text] Catechols react chemoselectively, in the presence of either alcohols, 1,2-diols, or simple phenols, with tert-butyl propynoate and with methyl propynoate to give 2-Boc-ethylidene (Bocdene) and 2-Moc-ethylidene (Mocdene) acetals, respectively, in 96-100% yields within 30 min at room temperature, provided that 150 mol % of DMAP is added. Cleavage of these acetals with pyrrolidine readily takes place (at room temperature!) in 95-100% yields. By taking advantage of the features of Bocdene acetals, novel catecholamine-related phosphate mimetics have been prepared.
authors.affiliation: Departament de Química Orgànica, Facultat de Química, Av. Diagonal 647, Universitat de Barcelona, 08028 Barcelona, Catalonia, Spain.
authors.forename: X
authors.initials: X
authors.lastname: Ariza
authors.forename: O
authors.initials: O
authors.lastname: Pineda
authors.forename: J
authors.initials: J
authors.lastname: Vilarrasa
authors.forename: G W
authors.initials: GW
authors.lastname: Shipps
authors.forename: Y
authors.initials: Y
authors.lastname: Ma
authors.forename: X
authors.initials: X
authors.lastname: Dai
mesh_terms: D000080:Acetals / Q000737:chemistry; D002384:Catalysis; D002395:Catecholamines / Q000737:chemistry*; D002396:Catechols / Q000737:chemistry*; D005563:Formic Acid Esters / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011759:Pyrrolidines / Q000737:chemistry
chemical_list: D000080:Acetals; D002395:Catecholamines; D002396:Catechols; D005563:Formic Acid Esters; D011759:Pyrrolidines; C000345:t-butyloxycarbonyl group; C032519:pyrrolidine