Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 79, Issue 12, Pages 5895-5902Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo500848a
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The addition of carbamoyl anions derived from N,N-disubstituted formamides and LDA to N-tert-butyl nitrones is described. The reaction was demonstrated with a variety of formamides and nitrones and provided a direct route to alpha-(N-hydroxy)amino amides. The use of a tert-leucinol derived chiral auxiliary on the nitrone provided products in good diastereoselectivity. Derivatization of the products by tert-butyl deprotection or N-deoxygenation was demonstrated.
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