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Synthesis 2019; 51(21): 4106-4112
DOI: 10.1055/s-0039-1690150
DOI: 10.1055/s-0039-1690150
paper
Evaluation of Amino Nitriles and an Amino Imidate as Organocatalysts in Aldol Reactions
We thank the Department of Chemistry, The University of York for financial support.Further Information
Publication History
Received: 13 June 2019
Accepted after revision: 18 July 2019
Publication Date:
08 August 2019 (online)

Abstract
The efficiency of l-valine and l-proline nitriles and a tert-butyl l-proline imidate as organocatalysts for the aldol reaction have been evaluated. l-Valine nitrile was found to be a syn-selective catalyst, while l-proline nitrile was found to be anti-selective, and gave products in modest to good enantioselectivities. tert-Butyl l-proline imidate was found to be a very efficient catalyst in terms of conversion of starting reagents to products, and gave good anti-selectivity. The enantioselectivity of the tert-butyl l-proline imidate was found to be good to excellent, with products being formed in up to 94% enantiomeric excess.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690150.
- Supporting Information
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