In 2022,Blair, Daniel J.; Chitti, Sriyankari; Trobe, Melanie; Kostyra, David M.; Haley, Hannah M. S.; Hansen, Richard L.; Ballmer, Steve G.; Woods, Toby J.; Wang, Wesley; Mubayi, Vikram; Schmidt, Michael J.; Pipal, Robert W.; Morehouse, Greg. F.; Palazzolo Ray, Andrea M. E.; Gray, Danielle L.; Gill, Adrian L.; Burke, Martin D. published an article in Nature (London, United Kingdom). The title of the article was 《Automated iterative Csp3-C bond formation》.Product Details of 821-41-0 The author mentioned the following in the article:
Fully automated synthetic chem. would substantially change the field by providing broad on-demand access to small mols. However, the reactions that can be run autonomously are still limited. Automating the stereospecific assembly of Csp3-C bonds would expand access to many important types of functional organic mols.1. Previously, methyliminodiacetic acid (MIDA) boronates were used to orchestrate the formation of Csp2-Csp2 bonds and were effective building blocks for automating the synthesis of many small mols., but they are incompatible with stereospecific Csp3-Csp2 and Csp3-Csp3 bond-forming reactions. Here authors report that hyperconjugative and steric tuning provide a new class of tetra-Me N-methyliminodiacetic acid (TIDA) boronates that are stable to these conditions. Charge d. anal. revealed that redistribution of electron d. increases covalency of the N-B bond and thereby attenuates its hydrolysis. Complementary steric shielding of carbonyl π-faces decreases reactivity towards nucleophilic reagents. The unique features of the iminodiacetic acid cage, which are essential for generalized automated synthesis, are retained by TIDA boronates. This enabled Csp3 boronate building blocks to be assembled using automated synthesis, including the preparation of natural products through automated stereospecific Csp3-Csp2 and Csp3-Csp3 bond formation. These findings will enable increasingly complex Csp3-rich small mols. to be accessed via automated assembly. In the experiment, the researchers used many compounds, for example, 5-Hexen-1-ol(cas: 821-41-0Product Details of 821-41-0)
5-Hexen-1-ol(cas: 821-41-0) is used in cyclization to a tetrahydropyran by phenylselenoetherification. It is also used as a building block in synthetic chemistry.Product Details of 821-41-0
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