Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 352, Issue 18, Pages 3438-3442Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201000495
Keywords
anionic rearrangement; contra-electronic carbolithiation; electron transfer; enol ethers; pyridine; reactive intermediates
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Funding
- FSU Research Foundation
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A previously reported anionic rearrangement of benzyl 2-pyridyl ethers can now be accessed by a distinct and unusual mechanism: addition of alkyllithium reagents to alpha-(2-pyridyloxy)-styrene triggers an anionic rearrangement to afford tertiary pyridyl carbinols. The process is explained by invoking a contra-electronic, pyridine-directed carbolithiation of the enol ether pi-system.
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