A flexible route to new spirodioxanes, oxathianes, and morpholines

This work describes a modular efficient route to 10-aza-4-thia-, 10-aza-4-oxa-, and 10-oxa-4-thia-1,7-dioxaspiro[5.5]undecanes. The synthetic pathway relies upon the iterative nucleophilic substitution of 1,3-dichloropropan-2-one O-benzyloxime by solketal derivatives. The oxime key-intermediates, su...

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Bibliographic Details
Published inTetrahedron Vol. 65; no. 21; pp. 4182 - 4189
Main Authors Goubert, Marlène, Canet, Isabelle, Sinibaldi, Marie-Eve
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 23.05.2009
Elsevier
Subjects
Chemical Sciences
Chemistry
Chemistry, Organic
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Organic chemistry
Physical Sciences
Preparations and properties
Science & Technology
CHEMISTRY
SPIROACETALS
ACID
ACCESS
CONSTRUCTION
STRATEGIES
Molecular flexibility
Purification
Spiroketal
Nitrogen heterocycle
Deprotection
Oxime
Morpholine derivatives
Oxygen heterocycle
Spiran
Nucleophilic substitution
Chemical synthesis
Acid medium
Oxygen nitrogen heterocycle
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Summary:This work describes a modular efficient route to 10-aza-4-thia-, 10-aza-4-oxa-, and 10-oxa-4-thia-1,7-dioxaspiro[5.5]undecanes. The synthetic pathway relies upon the iterative nucleophilic substitution of 1,3-dichloropropan-2-one O-benzyloxime by solketal derivatives. The oxime key-intermediates, submitted to an acidic deprotection–spiroacetalization process, afforded these original spiroketal compounds in three steps, few purifications, and very good yields. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2009.03.044