Diastereoselective Pictet-Spengler reactions of a tethered 2-aminoimidazole

Sudhir R. Shengule; Peter Karuso

doi:10.1071/CH13346

Diastereoselective Pictet-Spengler reactions of a tethered 2-aminoimidazole

Sudhir R. Shengule, Peter Karuso^*

^*Corresponding author for this work

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

2 Citations (Scopus)

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.

Original language	English
Pages (from-to)	184-191
Number of pages	8
Journal	Australian Journal of Chemistry
Volume	67
Issue number	2
DOIs	https://doi.org/10.1071/CH13346
Publication status	Published - 2014

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10.1071/CH13346

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AU - Karuso, Peter

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AB - 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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JF - Australian Journal of Chemistry

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ER -

Diastereoselective Pictet-Spengler reactions of a tethered 2-aminoimidazole

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