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

Woo Baeg Choi, Hywyn R.O. Churchill, Joseph E. Lynch, R. P. Volante, Paul J. Reider, Ichiro Shinkai, Deborah K. Jones, Dennis C. Liotta

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Abstract

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 °C in 5-6 h. Under the same conditions the (S) isomer 4B did not undergo decarboxylation and with further heating to 120 °C gave mainly the ring-opened decomposition product 6 along with unidentified decomposition products. A mechanistic rationale for this unusual reactivity profile is provided.

Original languageEnglish (US)
Pages (from-to)8367-8370
Number of pages4
JournalJournal of Organic Chemistry
Volume60
Issue number26
DOIs
StatePublished - Dec 1 1995
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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    Choi, W. B., Churchill, H. R. O., Lynch, J. E., Volante, R. P., Reider, P. J., Shinkai, I., Jones, D. K., & Liotta, D. C. (1995). An Unusual Stereoselective Decarboxylation: A Key Reaction to an Important Intermediate for Carbapenem Antibiotics. Journal of Organic Chemistry, 60(26), 8367-8370. https://doi.org/10.1021/jo00131a010