ArticleBeilstein journal of organic chemistry2025
Development and mechanistic studies of calcium-BINOL phosphate-catalyzed hydrocyanation of hydrazones.
Article in Beilstein journal of organic chemistry, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.
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2 citing papers in PubMed.
- A novel Ca(II) coordination polymer with 3-(3-carboxyphenyl)-isonicotinic acid: design, DFT analysis, and catalytic efficiency.BMC chemistry · 2026Article
- New advances in asymmetric organocatalysis II.Beilstein journal of organic chemistry · 2025Article
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Abstract
Asymmetric hydrocyanation of hydrazones, catalyzed by a calcium-BINOL phosphate complex, has been studied for the first time both experimentally and computationally with DFT methods. A full catalytic cycle for the enantioselective synthesis of α-hydrazinonitriles is proposed based on insights gained from DFT calculations. Trimethylsilyl cyanide (TMSCN) has been used as a sacrificial cyanide source. We found that isocyanide (rather than cyanide) is a preferred coordination to calcium during the catalytic cycle, while the active catalyst prefers a side-on coordination of cyanide. The configuration-determining step is a hydrocyanation via a calcium isocyanide complex, whereas the rate-limiting step is that which recovers the calcium catalyst and replaces the TMS-bound product from the catalyst. While our experimental data demonstrate enantioselectivity values as high as 89% under certain conditions, the overall enantioselectivity achieved with the calcium catalyst remains modest, mainly due to competing pathways for the
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