We are delighted to announce the recent publication of our collaborative research titled “Stereoselectivity and reactivity of the sodium borohydride reduction of 2-X-cyclohexanones”<\/p>\n\n\n\n
Our research group delved into the stereoselectivity and reactivity of the sodium borohydride reduction of 2-X-cyclohexanones (X=H, Cl, Br). Combining competitive experiments with density functional theory calculations, we uncovered that the hydride addition follows a late transition state where the C\u2013H bond is on the brink of formation. Interestingly, our data pointed out that the reaction barrier recedes when moving from the 2-halocyclohexanones to the unsubstituted cyclohexanone. This trend mirrors the relative reactivities observed in our competitive experiments. Moreover, we proudly introduce a comprehensive protocol to effectively model the axial\u2013equatorial facial selectivity of hydride addition to the carbonyl group when substituted with a neighboring polar group. Our findings emphasize the pivotal role of implicit solvation combined with an explicit solvent molecule to achieve the experimental stereoselective formation of the cis product.<\/p>\n\n\n\n
A commendable effort was made by all authors involved. Special mention to Daniela Rodrigues Silva.<\/strong><\/p>\n\n\n\n Our sincere gratitude to every collaborator on this project: Lucas A. Zeoly, Pascal Vermeeren, Trevor A. Hamlin, and C\u00e9lia Fonseca Guerra. special thanks to Matheus for this very interesting work and for all the years we are collaborating already.<\/p>\n\n\n\n