Issue 18, 2024

Exploiting natural complexity for substrate controlled regioselectivity and stereoselectivity in tantalum catalysed hydroaminoalkylation

Abstract

Naturally occurring and structurally diverse alkene-containing substrates, terpenes, provided a platform for establishing chemo-, regio-, and diastereoselective reactivity in tantalum catalysed hydroaminoalkylation. Naturally derived 1,3-butadienes revealed the unique regio- and diastereoselective (Z)-1,4-addition products accessible from isoprene and β-myrcene by hydroaminoalkylation. Selective terpene functionalisation, within an industrially produced turpentine mixture, demonstrates functionalisation specificity of β-pinene and limonene. Lastly, sesquiterpene functionalisation using β-caryophyllene and humulene provide rare examples of trisubstituted alkene reactivity in hydroaminoalkylation, by leveraging strain-release and stereoelectronic effects to control chemoselectivity. As a result of these reactivity studies using natural substrates, new tools for understanding alkene electronic, strain, and stereoelectronic effects on chemo- and diastereoselectivity outcomes have revealed new mechanistic insights into hydroaminoalkylation.

Graphical abstract: Exploiting natural complexity for substrate controlled regioselectivity and stereoselectivity in tantalum catalysed hydroaminoalkylation

Supplementary files

Article information

Article type
Paper
Submitted
02 Apr 2024
Accepted
06 Jun 2024
First published
30 Aug 2024

Green Chem., 2024,26, 9729-9736

Exploiting natural complexity for substrate controlled regioselectivity and stereoselectivity in tantalum catalysed hydroaminoalkylation

C. H. M. Zheng, B. E. Nadeau, H. L. Trajano and L. L. Schafer, Green Chem., 2024, 26, 9729 DOI: 10.1039/D4GC01614A

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