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3-Fluoro-2,4-dioxa-7-aza-3-phosphadecalin 3-Oxides as Rigid Acetylcholine Mimetics: Conformational Analysis and Direct Evidence of the Anomeric Effect

✍ Scribed by Stefan Furegati; Martin Binder; Anthony Linden; Peter Rüedi

Publisher
John Wiley and Sons
Year
2006
Tongue
German
Weight
384 KB
Volume
89
Category
Article
ISSN
0018-019X

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✦ Synopsis

Conformational analyses of the P(3)-axially and P(3)-equatorially F-substituted (AE)-cis-and (AE)trans-2, 4-dioxa-7-aza-3-phosphadecalin 3-oxides (3-fluoro-2,4-dioxa-7-aza-3-phosphabicyclo[4.4.0]decane 3-oxides) were performed. The results are based on independent studies in both solution and the solid state by 1 H-and 31 P-NMR experiments and computational and X-ray crystallographic data. As expected, the axial epimers adopt neat double-chair conformations in solution and in the crystal. Due to the anomeric effect of the electron withdrawing F-substituent, the 2,4-dioxa-3-phospha moiety in the equatorial epimers adopts a mixture of conformations in solution, mainly chair and twist-boat; whereas a neat twist-boat (trans-isomer) and the unusual envelope conformation (cis-isomer) were detected in the solid state. This is the first report of a straight visualization of these conformations and the impact of the anomeric effect in such systems.

📜 SIMILAR VOLUMES

2,4-Dioxa-7-aza-, 2,4-Dioxa-8-aza-, and
2,4-Dioxa-7-aza-, 2,4-Dioxa-8-aza-, and 2,4-Dioxa-9-aza-3-phosphadecalins as Rigid Acetylcholine Mimetics: Syntheses and Characterization
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Synthesis and Characterization of Enanti
Synthesis and Characterization of Enantiomerically Pure cis- and trans-3-Fluoro-2,4-dioxa-9-aza-3-phosphadecalin 3-Oxides as Acetylcholine Mimetics and Inhibitors of Acetylcholinesterase
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## Abstract The title compounds, the __P(3)__‐axially and __P(3)__‐equatorially substituted __cis__‐ and __trans__‐configured 9‐benzyl‐3‐fluoro‐2,4‐dioxa‐9‐aza‐3‐phosphadecalin 3‐oxides (=9‐benzyl‐3‐fluoro‐2,4‐dioxa‐9‐aza‐3‐phosphabicyclo[4.4.0]decane 3‐oxides=7‐benzyl‐2‐fluorohexahydro‐4__H__‐1,3,

Synthesis and Characterization of Enanti
Synthesis and Characterization of Enantiomerically Pure cis- and trans-3-Fluoro-2,4-dioxa-8-aza-3-phosphadecalin 3-Oxides as γ-Homoacetylcholine Mimetics and Inhibitors of Acetylcholinesterase
✍ Christian Clerc; Peter Rüedi 📂 Article 📅 2012 🏛 John Wiley and Sons 🌐 German ⚖ 647 KB

The title compounds, the P(3)-axially and P(3)-equatorially substituted cis-and trans-configured 8benzyl-3-fluoro-2,4-dioxa-8-aza-3-phosphadecalin 3-oxides (¼ 8-benzyl-3-fluoro-2,4-dioxa-8-aza-3-phosphabicyclo[4.4.0] [5,4-c]pyridine 2-oxides) were prepared (ee > 98%) and fully characterized (Schemes