- A practical method for building linear and cyclic triamines from (2-trimethylsilyl)ethanesulfonamides (SES-amides)
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SES-chloride has been obtained in higher yield and purity by improving Weinreb's original procedure, allowing efficient access to the primary SES-amide. Linear triamines can be built conveniently from the SES-amide in high yields, with the potential for orthogonal protection. The modified Richman-Atkins cyclisation of SES-amides allows access to novel biologically interesting triazamacrocycles with combinations of three-, four-, five- and six-carbon bridges within the ring. Purification of the free macrocyclic amines by distillation greatly simplifies the workup, increasing the practicability of multi-gram scale synthesis. Although CsF sometimes provided undesirably low yields in the deprotection step, alternative fluoride sources were found to be unsuitable for the deprotection of SES-triazamacrocycles.
- Parker, Laurie L.,Gowans, Nicholas D.,Jones, Stephen W.,Robins, David J.
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- Total synthesis and absolute configuration of the natural amino acid tetrahydrolathyrine
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(Chemical Equation Presented) The natural product tetrahydrolathyrine has been synthesized through an iminoiodane-mediated aziridination of a (2S)-allylglycinol derivative, which provided a 2:3 mixture of diastereoisomers. One of these diastereoisomers wa
- Benohoud, Meryem,Leman, Loic,Cardoso, Silvia H.,Retailleau, Pascal,Dauban, Philippe,Thierry, Josiane,Dodd, Robert H.
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supporting information; experimental part
p. 5331 - 5336
(2009/12/03)
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- Sequential aza-Baylis-Hillman/ring closing metathesis/aromatization as a novel route for the synthesis of substituted pyrroles
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A new route to diverse 2-substituted-3-methoxycarbonyl pyrroles has been developed. Diverse SES protected α-methylene β-aminoesters were obtained by a 3-component aza-Baylis-Hillman reaction. Diversity arose from the aryl aldehydes which can be used in th
- Declerck, Valerie,Ribiere, Patrice,Martinez, Jean,Lamaty, Fredereric
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p. 8372 - 8381
(2007/10/03)
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- Scope and limitations in sulfur ylide mediated catalytic asymmetric aziridination of imines: Use of phenyldiazomethane, diazoesters and diazoacetamides
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Imine aziridination using diazo-compounds and catalytic quantities of metal salts and sulfides has been investigated. A range of imines derived from benzaldehyde bearing electron-withdrawing groups (N-Ts,N-SO2CH2CH2SiMesu
- Aggarwal,Ferrara,O'Brien,Thompson,Jones,Fieldhouse
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p. 1635 - 1643
(2007/10/03)
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