Rearrangement of Spirocyclic Oxindoles with Lithium Amide Bases
- 11 September 2008
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 10 (20) , 4441-4444
Abstract
Spirocyclohexa-2,5-dienes were shown to rearrange at -40 degrees C, when treated with 1 equiv of LDA. Alkyl halides and aldehydes then reacted with the resulting phenanthridinone lithium enolate intermediates, with distinct regioselectivities and high diastereocontrol, to afford functionalized dearomatized phenanthridinones which were elaborated further. A mechanistic scheme involving a diisopropylamine-mediated proton transfer was proposed to rationalize the rearrangement.Keywords
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