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Amino acid-derived enaminones: a study in ring formation providing valuable asymmetric synthons.

ABSTRACT: A new reaction for the preparation of enaminones has been discovered. This method employs beta-amino acids as starting materials to allow diversification as well as incorporation of chirality. The beta-amino acids, once converted to ynones, are readily cyclized to the desired six-membered enaminone via a two-step, one-pot protocol. Although disguised as a 6-endo-dig cyclization, the reagents employed in the transformation play a direct role in bond making and bond breaking, thus changing the mode of addition.

SUBMITTER: Turunen BJ

PROVIDER: S-EPMC2596606 | biostudies-literature | 2006 Jul

REPOSITORIES: biostudies-literature

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Amino acid-derived enaminones: a study in ring formation providing valuable asymmetric synthons.

Turunen Brandon J BJ Georg Gunda I GI

Journal of the American Chemical Society 20060701 27

A new reaction for the preparation of enaminones has been discovered. This method employs beta-amino acids as starting materials to allow diversification as well as incorporation of chirality. The beta-amino acids, once converted to ynones, are readily cyclized to the desired six-membered enaminone via a two-step, one-pot protocol. Although disguised as a 6-endo-dig cyclization, the reagents employed in the transformation play a direct role in bond making and bond breaking, thus changing the mod ...[more]

PMID: 16819843

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