Spirocyclic Oxetanes: Synthesis and Properties

Wormholes through chemical space: Spirocyclic oxetanes are described as analogues of morpholine and also as topological siblings of their carbonyl counterparts. They are particularly promising in terms of both their physicochemical properties and the ease with which they can be grafted onto molecula...

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Published inAngewandte Chemie International Edition Vol. 47; no. 24; pp. 4512 - 4515
Main Authors Wuitschik, Georg, Rogers-Evans, Mark, Buckl, Andreas, Bernasconi, Maurizio, Märki, Moritz, Godel, Thierry, Fischer, Holger, Wagner, Björn, Parrilla, Isabelle, Schuler, Franz, Schneider, Josef, Alker, André, Schweizer, W. Bernd, Müller, Klaus, Carreira, Erick M.
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 02.06.2008
WILEY‐VCH Verlag
Wiley
Subjects
carbonyl compounds
Chemistry
Chemistry, Multidisciplinary
Cyclization
Ethers, Cyclic - chemical synthesis
Ethers, Cyclic - chemistry
heterocycles
morpholine
Morpholines
oxetanes
Physical Sciences
Science & Technology
Solubility
spiro compounds
morpholine
oxetanes
heterocycles
carbonyl compounds
spiro compounds
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ISSN1433-7851
1521-3773
1521-3773
DOI10.1002/anie.200800450

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Summary:Wormholes through chemical space: Spirocyclic oxetanes are described as analogues of morpholine and also as topological siblings of their carbonyl counterparts. They are particularly promising in terms of both their physicochemical properties and the ease with which they can be grafted onto molecular structures. The data collected highlight oxetanes as both the hydrophilic sister of a gem‐dimethyl unit and the carbonyl group's lipophilic brother.
Bibliography:istex:4BC1A7B69B4635246C67F527F5C260EDACF0E1B3
ark:/67375/WNG-7JZD61V1-0
F. Hoffmann-La Roche AG
ArticleID:ANIE200800450
We thank F. Hoffmann-La Roche AG for support of this research. We are indebted to Frank Senner and Pia Warga for their great dedication in measuring the physicochemical data described herein.
We thank F. Hoffmann‐La Roche AG for support of this research. We are indebted to Frank Senner and Pia Warga for their great dedication in measuring the physicochemical data described herein.
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ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.200800450