Ring expansion/homologation-aldehyde condensation cascade using tert-trihalomethylcarbinols

J. R. Falck, Anyu He, L. Manmohan Reddy, Abhijit Kundu, Deb K. Barma, A. Bandyopadhyay, Sukanta Kamila, Radha Akella, Romain Bejot, Charles Mioskowski

Research output: Contribution to journalArticle

20 Scopus citations

Abstract

Treatment of cyclic tert-trihalomethylcarbinols with CrCl2 in THF/HMPA in the presence of aryl or aliphatic aldehydes initiates a cascade sequence of one carbon ring expansion-olefination affording conjugated exocyclic ketones. Acyclic tert-trihalomethylcarbinols undergo a comparable cascade of one carbon homologation-olefination.

Original languageEnglish (US)
Pages (from-to)4645-4647
Number of pages3
JournalOrganic Letters
Volume8
Issue number20
DOIs
Publication statusPublished - Sep 28 2006

    Fingerprint

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Falck, J. R., He, A., Manmohan Reddy, L., Kundu, A., Barma, D. K., Bandyopadhyay, A., ... Mioskowski, C. (2006). Ring expansion/homologation-aldehyde condensation cascade using tert-trihalomethylcarbinols. Organic Letters, 8(20), 4645-4647. https://doi.org/10.1021/ol061953q