Intriguing Influence of the Solvent on the Regioselectivity of Sulfoxide Thermolysis in β-Amino-α-sulfinyl Esters

The sulfoxide thermolysis of the diastereoisomeric methyl (3R,4aS,10aR)‐6‐methoxy‐1‐methyl‐3‐(phenylsulfinyl)‐1,2,3,4,4a,5,10,10a‐octahydrobenzo[g]quinoline‐3‐carboxylates 3a and 3′b in toluene yields, by loss of benzenesulfenic acid, an almost 1 : 1 mixture of the vinylogous urethane 2b and the iso...

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Bibliographic Details
Published inHelvetica chimica acta Vol. 85; no. 5; pp. 1399 - 1406
Main Authors Bänziger, Markus, Klein, Solange, Rihs, Grety
Format Journal Article
LanguageEnglish
Published Basel Verlag Helvetica Chimica Acta 01.05.2002
Wiley
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
CARBONYL-COMPOUNDS
SULFENYLATIONS
SYNTHETIC REACTIONS
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Summary:The sulfoxide thermolysis of the diastereoisomeric methyl (3R,4aS,10aR)‐6‐methoxy‐1‐methyl‐3‐(phenylsulfinyl)‐1,2,3,4,4a,5,10,10a‐octahydrobenzo[g]quinoline‐3‐carboxylates 3a and 3′b in toluene yields, by loss of benzenesulfenic acid, an almost 1 : 1 mixture of the vinylogous urethane 2b and the isomeric α‐aminomethyl enoate 2a. When this elimination is performed in acetic acid, the enoate 2a is formed rather selectively. The same solvent effects on the regioselectivity of the elimination of benzenesulfenic acid are observed with a simple sulfoxide of ethyl piperidine‐3‐carboxylate (7).
Bibliography:ark:/67375/WNG-N31VPQB1-6
ArticleID:HLCA1399
istex:99DEA47702753A41F72E42836E965FFC2C92DB32
ISSN:0018-019X
1522-2675
DOI:10.1002/1522-2675(200205)85:5<1399::AID-HLCA1399>3.0.CO;2-R