A Direct Approach to Orthogonally Protected α-Amino Aldehydes
作者:Richard Lamb、Vincent L. Revil-Baudard、Samir Z. Zard
DOI:10.1021/acs.orglett.9b02237
日期:2019.8.16
O-Neopentyl-xanthate 19 bearing a masked α-amino aldehyde, with the two functional groups orthogonallyprotected, reacts cleanly with many functional alkenes. The radical addition–transfer furnishes densely functionalized adducts that can be further transformed into an array of amino-substituted carbocycles and heteroaromatics. They are also easily converted into imidazolones.
A Practical Route to Cyclobutanols and Fluorocyclobutanes
作者:Vincent L. Revil‐Baudard、Samir Z. Zard
DOI:10.1002/hlca.202100106
日期:2021.9
1-[(Ethoxycarbonothioyl)sulfanyl]cyclobutyl acetate (xanthate 7) was found to add to electronically unbiased alkenes and to certain heteroarenes. In the latter case, this corresponds to a variant of the Minisci reaction and allows the late-stage modification of biologically active substances. Saponification of the acetate furnishes the corresponding cyclobutanols, which, in the case of the nicotine
S-(3-Chloro-2-oxo-propyl)-O-ethyl xanthate: a linchpin radical coupling agent for the synthesis of heterocyclic and polycyclic compounds
作者:Olga Bergeot、Camilla Corsi、Myriem El Qacemi、Samir Z. Zard
DOI:10.1039/b514509k
日期:——
The preparation and use of S-(3-chloro-2-oxo-propyl)-O-ethyl xanthate to directly introduce an α-chloroketone motif is described, along with applications for the synthesis of heterocyclic and polycyclic structures.
Ultrasound-assisted one-pot three-component synthesis of new isoxazolines bearing sulfonamides and their evaluation against hematological malignancies
作者:Aicha Talha、Cécile Favreau、Maxence Bourgoin、Guillaume Robert、Patrick Auberger、Lahcen EL Ammari、Mohamed Saadi、Rachid Benhida、Anthony R. Martin、Khalid Bougrin
DOI:10.1016/j.ultsonch.2021.105748
日期:2021.10
regioselective 1,3-dipolar cycloaddition. The present methodology capitalized on trichloroisocyanuric acid (TCCA) as a safe and ecological oxidant and chlorinating agent for the in-situ conversion of aldehydes to nitrileoxides in the presence of hydroxylamine hydrochloride, under ultrasound activation. These nitrileoxides could be engaged in 1,3-dipolar cycloadditionreactions with various alkene to
A versatile strategy for the α-substitution of enones through the formal fusion between enones and unactivated alkenes is described. It relies on the formation and use of α-xanthyl-β-hydroxy ketones, which can be considered as synthetic equivalents of the high energy and difficult to tame alkenyl radicals. The process, which can often be accomplished one-pot, could be extended in one case to an α,β-unsaturated