One-Pot Multistep Synthesis of Trisubstituted Alkenes from N-Tosylhydrazones and Alcohols

A one-pot procedure for the synthesis of trisubstituted alkenes from N-tosylhydrazones and alcohols is reported. This procedure combines the aerobic oxidation reaction and Wittig reaction in one pot, which avoids using of environmentally toxic oxidants and isolation of the intermediates. The simple...

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Bibliographic Details
Published inSynthesis (Stuttgart) Vol. 46; no. 17; pp. 2353 - 2361
Main Authors Sha, Qiang, Wei, Yunyang
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.09.2014
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Wittig reaction
ENANTIOSELECTIVE SYNTHESIS
SELECTIVE OLEFINATION
CARBONYL-COMPOUNDS
PHOSPHORUS YLIDES
alkenes
ETHYL DIAZOACETATE
GENERATED DIAZO-COMPOUNDS
PORPHYRIN-CATALYZED OLEFINATION
ALDEHYDE-OLEFINATION
STEREOSELECTIVE-SYNTHESIS
diazo compounds
hydrazones
EPOXIDATION-ISOMERIZATION
olefination
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Summary:A one-pot procedure for the synthesis of trisubstituted alkenes from N-tosylhydrazones and alcohols is reported. This procedure combines the aerobic oxidation reaction and Wittig reaction in one pot, which avoids using of environmentally toxic oxidants and isolation of the intermediates. The simple procedure makes it very attractive for the synthesis of trisubstituted alkenes when alcohols are used as starting materials. A variety of trisubstituted alkenes as well as trifluoromethyl-substituted alkenes were obtained in moderate to good yields (up to 84%) with good E-selectivity (up to 99%).
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0034-1378231