Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 134, Issue 36, Pages 14764-14771Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja306276w
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Funding
- Arkansas Biosciences Institute
- National Science Foundation [CHE 1011788]
- National Institutes of Health [P30 RR031154, GM103450]
- NSF-REU [CHE 0851505]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [0851505, 1263119] Funding Source: National Science Foundation
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1011788] Funding Source: National Science Foundation
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In diethyl ether, N-Boc-2-lithio-2-arylpiperidines have been found to be configurationally stable at -80 degrees C, whereas N-Boc-2-lithio-2-arylpyrrolidines are configurationally stable at -60 degrees C. Several tertiary benzylic carbanions derived from enantioenriched 2-aryl heterocycles have been successfully alkylated or acylated with little to no loss of enantiopurity. The scope of the reactions has been explored. The enantiomerization dynamics of N-Boc-2-lithio-2-phenylpyrrolidine and N-Boc-2-lithio-2-phenylpiperidine have been studied in the presence of different solvents and achiral ligands.
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