Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 14, Issue 27, Pages 6457-6462Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c6ob01084a
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Funding
- National Natural Science Foundation of China [21102089]
- Natural Science Program of Shanghai [16ZR1413800]
- Shanghai University of Engineering Science [2012td09, nhrc-2015-09]
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We report a diastereoselective Mannich-type reaction of alpha-alkyl, alpha-aryl, and alpha-vinyl fluoroacetates with N-tert-butylsulfinyl imines. This method provides a powerful means to access a broad range of highly functionalized beta-amino acids containing alpha-fluorinated quaternary stereogenic carbon centers. We also show that the stereochemical outcome of the present reaction is highly dependent on the steric and electronic properties of the fluorocarbon nucleophiles. This protocol uses readily available starting materials, tolerates a variety of functional groups, and is operationally simple.
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