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Asymmetric organocatalytic synthesis of chiral homoallylic amines

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posted on 2025-03-14, 10:56 authored by Andrei MalkovAndrei Malkov, Nikolay Kondratyev

In recent decades, the chiral allylation of imines emerged as a key methodology in the synthesis of alkaloids and natural products with 4-, 5- and 6-membered cyclic amine motifs. Initially reliant on stoichiometric reagents, synthetic chemists predominantly used N-substituted chiral imines, organometallic chiral reagents and achiral reagents with an equimolar chiral controller. However, recent years have witnessed the rise of asymmetric transition-metal catalysts and, importantly, organocatalytic allylation, reshaping the landscape of modern synthetic chemistry. This review explores the latest developments in the asymmetric allylation of imines, encompassing cutting-edge advances in hydrogen-bond catalysis and non-classical approaches. Furthermore, practical examples showcasing the application of these innovative methodologies in total synthesis are presented.

History

School

  • Science

Published in

Beilstein Journal of Organic Chemistry

Volume

20

Pages

2349 - 2377

Publisher

Beilstein-Institut

Version

  • VoR (Version of Record)

Rights holder

© Kondratyev and Malkov

Publisher statement

This is an open access article licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-journals.org/bjoc/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this article could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material

Acceptance date

2024-08-30

Publication date

2024-09-16

Copyright date

2024

ISSN

1860-5397

eISSN

1860-5397

Language

  • en

Depositor

Prof Andrei Malkov. Deposit date: 16 September 2024

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