Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 133, Issue 25, Pages 9716-9719Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja2039248
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Funding
- NIGMS [GM-64451]
- NSF [DBI0619576]
- LaMattina
- AstraZeneca
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [0923264] Funding Source: National Science Foundation
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The Pd-catalyzed cross-coupling of racemic tertiary allylic carbonates and allylboronates is described. This reaction generates all-carbon quaternary centers in a highly regioselective and enantioselective fashion. The outcome of these reactions is consistent with a process that proceeds by way of 3,3'-reductive elimination of bis(eta(1)-allyl)palladium intermediates. Strategies for distinguishing the product alkenes and application to the synthesis of (+)-alpha-cuparenone are also described.
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