Chemists from the National University of Singapore have developed an innovative iron-based catalyst that enables the sustainable synthesis of highly sought-after Z-alkenes, opening new doors for drug discovery and other applications.
That is an incredible feat to overcome
The sustainable synthesis of trisubstituted Z-alkenes has been a long-standing problem in chemical manufacture. Such compounds are the essential leadin structures of bioactive agents and important substrates of many stereospecific reaction.
Historically, the Z-isomers of these alkenes have been challenging to access as they are not thermodynamically favored relative to their E forms. There is, therefore, a large lack of available data in the literature on these compounds and it has restricted the blatant inquiry and utilization of these compounds.
But, researchers from the National University of Singapore have come up with a new method that solves this problem. With the help of a cheap and commercially available bisphosphine-iron catalyst, they have developed a kinetically controlled catalytic process to access only the desired Z-isomers.
An Adaptable And Scalable Solution
This new approach created by the researchers is incredibly versatile and sustainable. Herein, we report the addition of many different aliphatic groups to an allene with exquisite site and Z-selectivity by merging allenes with sp3-hybridized organohalides or organozinc reagents.
The critical thinking in terms of this multicomponent strategy has enabled us not only to develop an efficient synthetic pathway for trisubstituted Z-alkenes but also to promote the use of cheap and environmentally friendly iron-based catalysts. This is an ecofriendly protocol and in addition, the use of iron as a transition metal is very attractive from economic and environmental point of view as it possesses non-toxicity, abundant nature, and cost effectiveness.
The utility of the approach was already demonstrated practically in the simplification of the preparation of a glucosylceramide synthase inhibitor, where bioactivity depends on its Z-configuration. This discovery will serve as a foundation to enhance the research and use of these coveted hydrocarbon compounds for various applications, including drug development.
Conclusion
This work in development of this iron-catalyzed method minimizes the synthetic steps for trisubstituted Z-alkenes, taking the field of chemical synthesis forward. In (1), the authors have not only overcome a long-standing obstacle but have also made such valuable compounds accessible in an easy way, thereby opening new avenues for their investigation and application in different fields of industry ranging from pharmaceuticals up to materials science. Beyond just breaking through an important barrier in the literature, this work has shown that low-cost and environmentally sustainable catalysts can push the envelope for the world’s largest industry finalmente realizing nearly four decades of phenomenal progress.
