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

Brandon J. Turunen; Gunda I. Georg

doi:10.1021/ja0609046

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

Brandon J. Turunen, Gunda I. Georg

Medicinal Chemistry

Research output: Contribution to journal › Article › peer-review

70 Scopus citations

Abstract

A new reaction for the preparation of enaminones has been discovered. This method employs β-amino acids as starting materials to allow diversification as well as incorporation of chirality. The β-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.

Original language	English (US)
Pages (from-to)	8702-8703
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	128
Issue number	27
DOIs	https://doi.org/10.1021/ja0609046
State	Published - Jul 12 2006

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abstract = "A new reaction for the preparation of enaminones has been discovered. This method employs β-amino acids as starting materials to allow diversification as well as incorporation of chirality. The β-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.",

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year = "2006",

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AU - Georg, Gunda I.

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Y1 - 2006/7/12

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AB - A new reaction for the preparation of enaminones has been discovered. This method employs β-amino acids as starting materials to allow diversification as well as incorporation of chirality. The β-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.

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IS - 27

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

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