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

doi:10.1021/ol061953q

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

Org Lett. 2006 Sep 28;8(20):4645-7. doi: 10.1021/ol061953q.

Authors

J R Falck¹, Anyu He, L Manmohan Reddy, Abhijit Kundu, Deb K Barma, A Bandyopadhyay, Sukanta Kamila, Radha Akella, Romain Bejot, Charles Mioskowski

Affiliation

¹ Department of Biochemistry, University of Texas Southwestern Medical Center, Dallas, Texas 75390, USA. j.falck@utsouthwestern.edu

Abstract

Treatment of cyclic tert-trihalomethylcarbinols with CrCl(2) 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.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

MeSH terms

Aldehydes / chemistry*
Cyclization
Methanol / chemistry*

Substances

Aldehydes
Methanol

Abstract

Publication types

MeSH terms

Substances

Grants and funding