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RESEARCH ARTICLE (Open Access)
Contents Vol 67(2)

Diastereoselective Pictet–Spengler Reactions of a Tethered 2-Aminoimidazole

Sudhir R. Shengule A and Peter Karuso A B
+ Author Affiliations
- Author Affiliations

A Department of Chemistry and Biomolecular Sciences, Macquarie University, Sydney, NSW 2109, Australia.

B Corresponding author. Email: peter.karuso@mq.edu.au

Australian Journal of Chemistry 67(2) 184-191 https://doi.org/10.1071/CH13346
Submitted: 3 July 2013  Accepted: 28 September 2013   Published: 8 November 2013

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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