2000
DOI: 10.1016/s0040-4020(00)00357-4
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The Photohydration of N -Glycosylpyridinium Salts and of Related Pyridinium N , O -Acetals

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Cited by 23 publications
(17 citation statements)
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“…[114] Ein alternativer Weg, Intermediate des Typs 68 in enantiomerenreiner Form zu erhalten, besteht darin, N-substituierte Pyridiniumionen einzusetzen, wobei der Substituent als Auxiliar dient. [115] Eine Anwendung findet sich in der formalen Synthese des hexaacylierten (+)-Trehazolamins, [116] dessen Umwandlung in (+)-Trehazolin bekannt ist. [117] Ein Nalkyliertes Pyridiniumsalz diente als Vorstufe in einer formalen Totalsynthese des (À)-Cephalotaxins.…”
Section: Aufsätzeunclassified
“…[114] Ein alternativer Weg, Intermediate des Typs 68 in enantiomerenreiner Form zu erhalten, besteht darin, N-substituierte Pyridiniumionen einzusetzen, wobei der Substituent als Auxiliar dient. [115] Eine Anwendung findet sich in der formalen Synthese des hexaacylierten (+)-Trehazolamins, [116] dessen Umwandlung in (+)-Trehazolin bekannt ist. [117] Ein Nalkyliertes Pyridiniumsalz diente als Vorstufe in einer formalen Totalsynthese des (À)-Cephalotaxins.…”
Section: Aufsätzeunclassified
“…In 1972, Kaplan, Pavlik, and Wilzbach1 showed that the irradiation of N ‐methylpyridinium chloride ( 1 a ) in H 2 O in the presence of base gave the bicyclic aziridine (±)‐ 2 a (Scheme ). Their communication went relatively unnoticed for nearly a quarter of a century until it was recognized that this transformation of the pyridinium ring provides a new and powerful approach to aminocyclopentanes with well‐defined substitution patterns 2, 7. Highly functionalized aminocyclopentanes are of considerable interest as precursors of glycosidase inhibitors8 and of carbocyclic analogues of nucleosides 9.…”
Section: Introductionmentioning
confidence: 99%
“…Opening of the three‐membered ring of compounds 2 by oxygen and sulfur nucleophiles is a key reaction on the way toward aminocyclopentitols 3, 4. Recently, the diastereomers ( 2 e ) resulting from the photohydration of α ‐ D ‐glucopyranosylpyridinium chloride ( 1 e ) were resolved after peracetylation into enantiopure bridged aziridines 7. Mariano et al5 have exploited the photohydration of the parent pyridinium ion ( 1 f , R=H) in strong acid.…”
Section: Introductionmentioning
confidence: 99%
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