Diastereoselective Pictet–Spengler Reactions of a Tethered 2-Aminoimidazole

Author:

Shengule Sudhir R.,Karuso Peter

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.

Publisher

CSIRO Publishing

Subject

General Chemistry

Cited by 2 articles. 订阅此论文施引文献 订阅此论文施引文献,注册后可以免费订阅5篇论文的施引文献,订阅后可以查看论文全部施引文献

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2. Reactions of Aldehydes and Ketones and their Derivatives;Organic Reaction Mechanisms · 2014;2018-01-05

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