An Unusual Stereoselective Decarboxylation: A Key Reaction to an Important Intermediate for Carbapenem Antibiotics

The dramatic difference in reactivity of the two diastereomeric acid esters 4A and 4B during decarboxylation has been thoroughly investigated, The (R) isomer 4A underwent decarboxylation to provide a 94:6 mixture of 5A and 5B at 80 degrees C in 5-6 h. Under the same conditions the (S) isomer 4B did...

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Published inJournal of organic chemistry Vol. 60; no. 26; pp. 8367 - 8370
Main Authors Choi, Woo-Baeg, Churchill, Hywyn R. O, Lynch, Joseph E, Volante, R. P, Reider, Paul J, Shinkai, Ichiro, Jones, Deborah K, Liotta, Dennis C
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.12.1995
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
FORMIC-ACID
UNIMOLECULAR DISSOCIATION CHANNELS
AM1
ACID MONOMER
ISOMERIZATION
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Summary:The dramatic difference in reactivity of the two diastereomeric acid esters 4A and 4B during decarboxylation has been thoroughly investigated, The (R) isomer 4A underwent decarboxylation to provide a 94:6 mixture of 5A and 5B at 80 degrees C in 5-6 h. Under the same conditions the (S) isomer 4B did not undergo decarboxylation and with further heating to 120 degrees C gave mainly the ring-opened decomposition product 6 along with unidentified decomposition products, A mechanistic rationale for this unusual reactivity profile is provided.
Bibliography:istex:45F3466C21E320783A4919305F75DAEDBEB00C1B
ark:/67375/TPS-27N16S62-K
ISSN:0022-3263
1520-6904
DOI:10.1021/jo00131a010