Journal
CHEMICAL SCIENCE
Volume 7, Issue 8, Pages 4985-4989Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c6sc01086e
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Funding
- NSF [CHE-1360634]
- NIH [GM-033049]
- Syngenta
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1360634] Funding Source: National Science Foundation
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Diorganocuprate(I) reagents derived from lithiated heterocycles and CuCN react with enantioenriched secondary propargyl bromides to give the corresponding propargylated heterocycles. While propargyl electrophiles typically undergo S(N)2' displacement, this transformation represents the first example of the reaction of hard carbanions with propargyl electrophiles in an S(N)2 fashion and occurs with excellent levels of stereoinversion. The new method was applied to the formal synthesis of (+)-frondosin B.
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