- Thermally induced substrate release via intramolecular cyclizations of Amino esters and Amino carbonates
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The relative cleavage of an alcohol from a panel of amino esters and amino carbonates via intramolecular cyclization was examined as a mechanism for substrate release. Thermal stability at 37 °C was observed only for the seven-membered ring progenitors. Applicability of the approach was illustrated by δ-lactam formation within a poly(dimethylsiloxane) microchannel for release of a captured fluorescent probe.
- Knipp, Ralph J.,Estrada, Rosendo,Sethu, Palaniappan,Nantz, Michael H.
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supporting information
p. 3422 - 3429
(2014/05/06)
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- Hydrolytic deallylation of N-allyl amides catalyzed by PdII complexes
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Hydrolytic deallylation of N-allyl amides to give amides and propanal can be achieved with PdII catalysts. The optimized catalyst consists of Pd(OCOCF3)2 and 1,3-bis(diphenylphosphanyl) propane (DPPP). Several kinds of open-chain N-allyl amides and N-allyl lactams undergo hydrolytic deallylation to give the corresponding amides and lactams in good to high yield. A mechanism which includes isomerization to enamides and subsequent hydrolysis is proposed. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
- Ohmura, Naoya,Nakamura, Asami,Hamasaki, Akiyuki,Tokunaga, Makoto
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supporting information; experimental part
p. 5042 - 5045
(2009/05/07)
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- A practical ruthenium-catalyzed cleavage of the allyl protecting group in amides, lactams, imides, and congeners
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A convenient methodology for the deprotection of N-allylic amide-like moieties was developed. The first examples accounting for the ruthenium-catalyzed deallylation of amides, lactams, imides, pyrazolidones, hydantoins, and oxazolidinones have been achieved by the sequential use of Grubbs carbene (isomerization step) and RuCl3 (oxidation step). A variety of substrates, including enantiopure multifunctional β- and γ-lactams, can be employed.
- Alcaide, Benito,Almendros, Pedro,Alonso, Jose M.
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p. 2874 - 2879
(2008/02/03)
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- Direct N-Allylation of Amides with 2-Allylisourea Catalyzed by Palladium(0)
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Direct N-allylation of amides catalyzed by palladium(0) complexes took place under neutral conditions by the use of 2-allylisourea as the allylating agent.
- Inoue, Yoshio,Taguchi, Masaaki,Hashimoto, Harukichi
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p. 2721 - 2722
(2007/10/02)
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