Stereocontrolled synthesis of 3-(ethoxycarbonyl)-4-hydroxy-2-isoxazoline-2-oxides. A new approach to the synthesis of 4-hydroxylated 2-isoxazolines

Treatment of 2-bromo aldehydes and ethyl nitroacetate with alumina without solvent, or in solution with a tertiary base, at room temperature gives the diastereoisomeric title compounds in fair yields by a tandem nitroaldol reaction-cyclization sequence opening a new route for the preparation of tran...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 56; no. 22; pp. 6258 - 6260
Main Authors Rosini, Goffredo, Marotta, Emanuela, Righi, Paolo, Seerden, Jean Paul
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.10.1991
Amer Chemical Soc
Subjects
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
Organic chemistry
Physical Sciences
Preparations and properties
Science & Technology
ORGANIC-SYNTHESIS
AMINO-SUGARS
CONJUGATED NITROALKENES
DERIVATIVES
ISOXAZOLINES
Stereoselectivity
Nitro compound
Five membered ring
Cyclization
Aluminium
Nitronate
Secondary alcohol
Aldehyde
Oxygen nitrogen heterocycle
Ylide
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Summary:Treatment of 2-bromo aldehydes and ethyl nitroacetate with alumina without solvent, or in solution with a tertiary base, at room temperature gives the diastereoisomeric title compounds in fair yields by a tandem nitroaldol reaction-cyclization sequence opening a new route for the preparation of trans and cis 4-hydroxylated 2-isoxazolines in a predictable way.
Bibliography:ark:/67375/TPS-8J9LH8TG-G
istex:D68815D1D1270AF3747445055568E2161EF326FC
ISSN:0022-3263
1520-6904
DOI:10.1021/jo00022a005