- Nucleophile-catalyzed additions to activated triple bonds. protection of lactams, imides, and nucleosides with MocVinyl and related groups
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Additions of lactams, imides, (S)-4-benzyl-1,3-oxazolidin-2-one, 2-pyridone, pyrimidine-2,4-diones (AZT derivatives), or inosines to the electron-deficient triple bonds of methyl propynoate, tert-butyl propynoate, 3-butyn-2-one, N-propynoylmorpholine, or
- Mola, Laura,Font, Joan,Bosch, Lluis,Caner, Joaquim,Costa, Anna M.,Etxebarria-Jardi, Gorka,Pineda, Oriol,De Vicente, David,Vilarrasa, Jaume
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p. 5832 - 5842
(2013/07/26)
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- Bocdene and mocdene derivatives of catechols and catecholamines.
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[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,Pineda,Vilarrasa,Shipps Jr.,Ma,Dai
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p. 1399 - 1401
(2007/10/03)
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