Keck asymmetric allylation in natural product synthesis: applications and developments (2018–2026)
- 1Department of Chemistry, Quaid-I-Azam University Islamabad 45320 Pakistan
- 2Department of Chemistry, Faculty of Science, Zagazig University Zagazig 44519 Egypt
- 3Department of Chemistry, Faculty of Science, Islamic University of Madinah Madinah 42351 Saudi Arabia
Abstract
Following our 2017 comprehensive review, this update highlights the evolving and pivotal role of the Ti–BINOL-catalyzed Keck asymmetric allylation in modern total synthesis. Highly regarded for its operational simplicity and outstanding enantiocontrol, the methodology still represents a cornerstone for the synthesis of optically active homoallylic alcohols and the assembly of complex molecular architectures. Herein, we review its application as a key stereodefining step in the recent syntheses of several structurally diverse and biologically active targets including (+)-ineleganolide, (+)-sieboldine A, ieodomycin derivatives, latrunculin B, (–)-melearoride A, PF1163B, cryptorigidifoliol G, cryptoconcatone I, and antarlides A–F. Besides traditional applications, this review also covers recent methodological advances to improve reaction efficiency, including the implementation of modified ligand frameworks and optimized additive systems. We also discuss frontier approaches that extend the classical scope of the reaction, with particular emphasis on emerging three-component asymmetric Tsuji–Trost allylations using chiral aldehydes and dual palladium catalysis.
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BibTeX
@article{zafar2026keck,
title = {{Keck asymmetric allylation in natural product synthesis: applications and developments (2018–2026)}},
author = {Kiran Zafar and Saba Bukhari and Aamer Saeed and Basant Farag and Sobhi M. Gomha and Hesham R. El-Seedi},
journal = {RSC advances},
year = {2026},
month = oct,
doi = {10.1039/d6ra08645d},
url = {https://europepmc.org/article/PMC/PMC13659809},
note = {CC BY-NC},
}
RIS
TY - JOUR
TI - Keck asymmetric allylation in natural product synthesis: applications and developments (2018–2026)
AU - Kiran Zafar
AU - Saba Bukhari
AU - Aamer Saeed
AU - Basant Farag
AU - Sobhi M. Gomha
AU - Hesham R. El-Seedi
PY - 2026
DA - 2026/10/13
JO - RSC advances
DO - 10.1039/d6ra08645d
UR - https://europepmc.org/article/PMC/PMC13659809
AB - Following our 2017 comprehensive review, this update highlights the evolving and pivotal role of the Ti–BINOL-catalyzed Keck asymmetric allylation in modern total synthesis. Highly regarded for its operational simplicity and outstanding enantiocontrol, the methodology still represents a cornerstone for the synthesis of optically active homoallylic alcohols and the assembly of complex molecular architectures. Herein, we review its application as a key stereodefining step in the recent syntheses of several structurally diverse and biologically active targets including (+)-ineleganolide, (+)-sieboldine A, ieodomycin derivatives, latrunculin B, (–)-melearoride A, PF1163B, cryptorigidifoliol G, cryptoconcatone I, and antarlides A–F. Besides traditional applications, this review also covers recent methodological advances to improve reaction efficiency, including the implementation of modified ligand frameworks and optimized additive systems. We also discuss frontier approaches that extend the classical scope of the reaction, with particular emphasis on emerging three-component asymmetric Tsuji–Trost allylations using chiral aldehydes and dual palladium catalysis.
SN - 2046-2069
ER -