- Taking advantage of lithium monohalocarbenoid intrinsic α-elimination in 2-MeTHF: controlled epoxide ring-openingen routeto halohydrins
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The intrinsic degradative α-elimination of Li carbenoids somehow complicates their use in synthesis as C1-synthons. Nevertheless, we herein report how boosting such an α-elimination is a straightforward strategy for accomplishing controlled ring-opening of epoxides to furnish the corresponding β-halohydrins. Crucial for the development of the method is the use of the eco-friendly solvent 2-MeTHF, which forces the degradation of the incipient monohalolithium, due to the very limited stabilizing effect of this solvent on the chemical integrity of the carbenoid. With this approach, high yields of the targeted compounds are consistently obtained under very high regiocontrol and, despite the basic nature of the reagents, no racemization of enantiopure materials is observed.
- Ielo, Laura,Miele, Margherita,Pillari, Veronica,Senatore, Raffaele,Mirabile, Salvatore,Gitto, Rosaria,Holzer, Wolfgang,Alcántara, Andrés R.,Pace, Vittorio
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supporting information
p. 2038 - 2043
(2021/03/16)
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- TRICYCLIC COMPOUNDS
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The present invention provides a compound of formula I or a pharmaceutically acceptable salt thereof; and its therapeutic uses. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.
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Paragraph 0741; 0742
(2014/06/25)
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- A straightforward and general access to α-phthalimido-α′- substituted propan-2-ones
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The regioselective ring opening of the commercially available N-(2,3-epoxypropyl)phthalimide with different nucleophiles, to obtain the corresponding phthalimidopropan-2-ols (including a challenging fluorohydrin) followed by the Dess-Martin periodinane ox
- Pace, Vittorio,Holzer, Wolfgang
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supporting information; experimental part
p. 5106 - 5109
(2012/10/08)
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