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Synthesis 2018; 50(12): 2394-2406
DOI: 10.1055/s-0036-1591567
DOI: 10.1055/s-0036-1591567
paper
Enantioselective Biginelli Reaction of Aliphatic Aldehydes Catalyzed by a Chiral Phosphoric Acid: A Key Step in the Synthesis of the Bicyclic Guanidine Core of Crambescin A and Batzelladine A
Further Information
Publication History
Received: 17 February 2018
Accepted after revision: 19 March 2018
Publication Date:
25 April 2018 (online)
Abstract
An efficient chiral phosphoric acid catalyzed Biginelli reaction for the synthesis of optically pure 4-alkyl-3,4-dihydropyrimidin-2-(1H)-ones has been developed, with a wide range of the desired products being obtained in moderate to high yields with good to excellent enantioselectivities (up to >99% ee after one recrystallization). The synthetic utility of this reaction is illustrated in various aliphatic bicyclic guanidine compounds, which is applied in the formal synthesis of the bicyclic guanidine core of crambescin A and batzelladine A.
Key words
Biginelli reaction - dihydropyrimidinone - aliphatic aldehydes - crambescin - batzelladineSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591567.
- Supporting Information
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