Bocdene and mocdene derivatives of catechols and catecholamines.
[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.
Ariza
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Departament de Química Orgànica, Facultat de Química, Av. Diagonal 647, Universitat de Barcelona, 08028 Barcelona, Catalonia, Spain.
Pineda
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O
Vilarrasa
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J
Shipps
G W
GW
Ma
Y
Y
Dai
X
X
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
D000080:Acetals; D002395:Catecholamines; D002396:Catechols; D005563:Formic Acid Esters; D011759:Pyrrolidines; C000345:t-butyloxycarbonyl group; C032519:pyrrolidine