Wiley-VCH Verlag, ChemInform, 16(34), 2003
Elsevier, Tetrahedron, 51(58), p. 10167-10171
DOI: 10.1016/s0040-4020(02)01363-7
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We have developed a versatile methodology to obtain α-amino ketones by acylation of methyl N-benzoyl-7-azabicyclo[2.2.1]heptane-1-carboxylate (1) with organolithium reagents. The reaction proceeds via a stable tetrahedral intermediate. When methyl ester 1 was treated under the same conditions but with a different work up procedure (careful addition of saturated NH4Cl), we observed by 1H NMR spectroscopy that a new compound had appeared in the crude reaction mixture corresponding to a hemiacetal.