Addition of organolithium reagents to Ahc methyl ester. An approach to new alpha-amino ketones
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Universidad de La Rioja
info
ISSN: 0040-4020
Any de publicació: 2002
Volum: 58
Número: 51
Pàgines: 10167-10171
Tipus: Article
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Resum
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. © 2002 Elsevier Science Ltd. All rights reserved.