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Updated: Jul 6, 2025

A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
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A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products

Published on: September 9, 2016

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1,10-seco-guaianolides的基于灾难选择性合的不对称总合成

Rodney A Fernandes1, Ravikant S Ranjan1

  • 1Department of Chemistry, Indian Institute of Technology Bombay Powai, Mumbai 400076, Maharashtra, India. rfernand@chem.iitb.ac.in.

Organic & biomolecular chemistry
|January 3, 2024
PubMed
概括

这项研究引入了一种新型的催化合反应,用于合成复杂的丁烯. 该方法有效地产生具有高立体化学控制的有价值的二次瓜亚诺化物.

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The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
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The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
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Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
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Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
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