A Facially-Selective Protonation Controls the Stereochemistry of a Key Intermediate in the Synthesis of 1β-Methylcarbapenems

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

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12 Scopus citations

Abstract

Investigation into the selectivity observed in the synthesis of 1β-methylcarbapenems was carried out by examining (1) the rotational barrier between the two possible ketene acetal conformations A and B and (2) the protonation of ketene acetal 3 to the mono acid product 2, using the MNDO Hamiltonian.

Original languageEnglish (US)
Pages (from-to)3749-3751
Number of pages3
JournalJournal of Organic Chemistry
Volume59
Issue number14
DOIs
StatePublished - Jul 1 1994
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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  • Cite this

    Jones, D. K., Liotta, D. C., Choi, W. B., Volante, R. P., Reider, P. J., Shinkai, I., Churchill, H. R. O., & Lynch, J. E. (1994). A Facially-Selective Protonation Controls the Stereochemistry of a Key Intermediate in the Synthesis of 1β-Methylcarbapenems. Journal of Organic Chemistry, 59(14), 3749-3751. https://doi.org/10.1021/jo00093a001