Dolors Fernández-Forner

Synthesis of 5-(sulfamoylmethyl)indoles

Abstract The synthesis of 5-(sulfamoylmethyl)indoles bearing a two-carbon chain at C-3 (aminoethyl, acetate, hydroxyethyl, ethyl) either by the Grandberg modification of the Fischer indolization or by intramolecular Heck reaction of suitable o -halotrifluoroacetanilides is reported.

NPE-resin, a new approach to the solid-phase synthesis of protected peptides and oligonucleotides I : Synthesis of the supports and their application to oligonucleotide synthesis.

Abstract The preparation of polymeric supports containing a base labile 2-(2-nitrophenyl) ethyl linkage and the attachment of protected nucleosides is described together with their application to oligonucleotide synthesis.

Solid-phase synthesis of 4-aminopiperidine analogues using the Alloc protecting group: an investigation of Alloc removal from secondary amines

Abstract A useful method for Alloc removal from secondary amines on solid-phase has been optimised. The use of Me 2 NH·BH 3 (40 equiv., 40 min) as scavenger of the allyl cations in a palladium-catalysed process with Pd[PPh 3 ] 4 leads to quantitative removal of the Alloc group without any allyl back alkylation. Other scavengers such as morpholine or PhSiH 3 are clearly inferior. Furthermore, this study has highlighted differences in the reaction kinetics of the deprotection step between secondary and primary amines such as those from α-amino acids.

Preparation of oligonucleotides containing dAICA using an unexpected side-reaction observed on a protected derivative of 2-aza-2′-deoxyinosine.

Abstract Attempts of synthesis of oligonucleotides containing 2-aza-2′-deoxyinosine protected with the N,N-diphenylcarbamoyl group are described. An unexpected behaviour of the protected nucleoside can be used for the introduction of dAICA in synthetic oligonucleotides.

BAL resin for the preparation of secondary amines

Although amino acids anchored through the amino function to BAL resins can not easily be released from the resin by treatment with neat trifluoroacetic acid, we have shown that secondary amines can be obtained from BAL resins using trifluoroacetic acid solutions.

Solid-phase syntheses of N-substituted carbamates. Reaction monitoring by gel-phase 13C NMR using a 13C enriched BAL-linker

Abstract The solid-phase synthesis of N -substituted carbamates using the tris(alkoxy)benzyl (BAL) resin is reported. The incorporation of the primary amine was carried out by reductive amination, which was followed by reaction with an alkyl succinimidyl carbonate prepared in situ from the alcohol and N,N ′-disuccinimidyl carbonate (DSC). Final cleavage with trifluoroacetic acid rendered the target compounds. Scope and limitations of these methods are discussed. The reactions were controlled by gel-phase 13 C NMR using a 13 C enriched BAL resin.