- N-Methyl Allylic Amines from Allylic Alcohols by Mitsunobu Substitution Using N-Boc Ethyl Oxamate
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We report the practical, scalable synthesis of a range of N-methyl allylic amines. Primary and secondary allylic alcohols underwent a regioselective Mitsunobu reaction with readily accessible N-Boc ethyl oxamate to deliver the corresponding N-Boc allylic amines, including in enantiopure form via stereospecific substitution. Subsequent N-methylation and Boc deprotection without chromatography yielded the amine products as hydrochloride salts. This method solves the problem of converting commercially available alcohols into often volatile N-methyl allylic amines, many of which have limited commercial availability.
- Van Veen, Branca C.,Wales, Steven M.,Clayden, Jonathan
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p. 8538 - 8543
(2021/06/30)
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- Signal-amplifying conjugated polymer-DNA hybrid chips
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Expand on that: Signal-amplifying DNA chips have been fabricated by a light-directed on-chip DNA synthesis on a thin film of a photostable conjugated polyoxadiazole derivative. The fluorescence signal from a hexachlorofluorescein- labeled target DNA was i
- Lee, Kangwon,Rouillard, Jean-Marie,Pham, Trinh,Gulari, Erdogan,Kim, Jinsang
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p. 4667 - 4670
(2008/02/08)
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- Convenient Synthesis of 3,4-methano-1,2,3,4-tetrahydroisoquinoline-3-carboxylic Acid and Its Derivatives as Doubly Constrained Nonproteinogenic Amino Acid Derivatives
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Three strategies for the synthesis of the novel, doubly constrained, 3,4-methano-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid and its derivatives were evaluated. Only cyclocondensation of the mono(triphenyl)phosphonium salt derived from 1,2-bis(bromomethyl)benzene with N-alkoxycarbonyloxamates in 1,2-dimethoxyethane in the presence of potassium carbonate and subsequent cyclopropanation with dimethylsulfoxonium methylide in dimethyl sulfoxide furnished suitable O-and N-protected derivatives of 3,4-methano-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid in a convenient way. A detailed 2D DQF-COSY and 2D NOESY NMR analysis of the rotational isomerism of the latter bicyclic amino acid derivatives was performed. Various O- and N-protection protocols were worked out to afford access to a whole range of new derivatives of the title amino acid, suitable for peptide synthesis.
- Czombos, Jozsef,Aelterman, Wim,Tkachev, Alexey,Martins, Jose C.,Tourwe, Dirk,Peter, Antal,Toeth, Geza,Fueloep, Ferenc,De Kimpe, Norbert
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p. 5469 - 5475
(2007/10/03)
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- N-Boc and N-Cbz ethyl oxamates: New Gabriel reagents
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N-Boc and N-CBz ethyl oxamates can be directly coupled with various halides under Gabriel conditions which afford the corresponding N-protected amines after mild deprotection with LiOH.
- Berree, Fabienne,Bazureau, Jean-Pierre,Michelot, Gwendal,Le Corre, Maurice
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p. 2685 - 2693
(2007/10/03)
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- N-Boc ethyl oxamate: A new nitrogen nucleophile for use in Mitsunobu reactions
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N-Boc ethyl oxamate can be directly coupled with primary and secondary alcohols under Mitsunobu conditions to afford various N-Boc mines after mild deprotection.
- Berree, Fabienne,Michelot, Gwendal,Le Corre, Maurice
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p. 8275 - 8276
(2007/10/03)
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