2004
DOI: 10.1002/mrc.1397
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Complete NMR elucidation of a novel trishomocubane hydantoin and its mono‐ and bis‐t‐Boc protected derivatives

Abstract: The syntheses of a novel trishomocubane hydantoin and its mono- and bis-protected t-Boc derivatives are described. The less nucleophilic N-3' nitrogen of the hydantoin ring is protected first when treated with di-tert-butyl dicarbonate (t-Boc anhydride), possibly owing to steric hindrance by the bulky trishomocubane cage skeleton. More basic conditions were required to form the bis-protected t-Boc hydantoin with the same reagent. The structures of these novel compounds were elucidated with 2D NMR techniques. T… Show more

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Cited by 15 publications
(28 citation statements)
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“…0 3,10 .0 5,9 ] undecane (trishomocubane) was first reported by Eaton et al [1]. As part of a project to synthesise pentacycloundecane derived cage amino acids [2][3][4][5], the synthesis of racemic trishomocubane hydantoin 2 [6] and the corresponding amino acid 3 was undertaken (see Fig. 1).…”
Section: Introductionmentioning
confidence: 97%
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“…0 3,10 .0 5,9 ] undecane (trishomocubane) was first reported by Eaton et al [1]. As part of a project to synthesise pentacycloundecane derived cage amino acids [2][3][4][5], the synthesis of racemic trishomocubane hydantoin 2 [6] and the corresponding amino acid 3 was undertaken (see Fig. 1).…”
Section: Introductionmentioning
confidence: 97%
“…This method, according to literature [11], should result in an improved yield compared to the conventional hydrolysis [5,12] of the unprotected hydantoins. Mono-Boc protection of the hydantoin at N-3 was reported before [6]. Although NMR elucidation of the pentacyclo-undecane cage system is well studied 1 School of Chemistry, University of KwaZulu-Natal, Durban 4001, South Africa.…”
Section: Introductionmentioning
confidence: 98%
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“…Protons on the cage are normally deshielded if a heteroatom of a side chain is positioned such that the electron rich heteroatom is in close proximity of the cage proton(s). [4,19,28,29] It is possible that the OH and NH 2 groups in 1 cause intramolecular hydrogen bond interactions. This will largely 'tie' the two groups together at room temperature.…”
Section: Resultsmentioning
confidence: 99%