Diastereoselective Pictet-Spengler reactions of a tethered 2-aminoimidazole

Sudhir R. Shengule, Peter Karuso

Research output: Contribution to journalArticleResearchpeer-review

Abstract

The diastereoselective Pictet-Spengler reaction of aminopropyl-2- aminoimidazole with enantiopure aldehydes has been investigated. With amino acid-derived aldehydes, anti stereochemistry is favoured, with a diastereoselectivity up to 92% achievable. The absolute stereochemistry of the products was determined through synthesis of a rigid derivative and from NMR data in combination with molecular modelling. The diastereoselectivity was shown to be dependent on the steric bulk of the amino acid side chain and independent of the nitrogen protecting group. Lewis acids catalysed the reaction but did not affect the diastereoselectivity.

LanguageEnglish
Pages184-191
Number of pages8
JournalAustralian Journal of Chemistry
Volume67
Issue number2
DOIs
Publication statusPublished - 2014

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Stereochemistry
Aldehydes
Amino Acids
Lewis Acids
Molecular modeling
Nitrogen
Nuclear magnetic resonance
Derivatives
2-aminoimidazole

Cite this

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abstract = "The diastereoselective Pictet-Spengler reaction of aminopropyl-2- aminoimidazole with enantiopure aldehydes has been investigated. With amino acid-derived aldehydes, anti stereochemistry is favoured, with a diastereoselectivity up to 92{\%} achievable. The absolute stereochemistry of the products was determined through synthesis of a rigid derivative and from NMR data in combination with molecular modelling. The diastereoselectivity was shown to be dependent on the steric bulk of the amino acid side chain and independent of the nitrogen protecting group. Lewis acids catalysed the reaction but did not affect the diastereoselectivity.",
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Diastereoselective Pictet-Spengler reactions of a tethered 2-aminoimidazole. / Shengule, Sudhir R.; Karuso, Peter.

In: Australian Journal of Chemistry, Vol. 67, No. 2, 2014, p. 184-191.

Research output: Contribution to journalArticleResearchpeer-review

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