ChemInform Abstract: A New Approach to β‐Fluoropyrroles Based on the Michael Addition of Isocyanomethylide Anions to α‐Fluoroalkenyl Sulfones and Sulfoxides.

Uno, Hidemitsu; Sakamoto, Katsuyoshi; Tominaga, Tamotsu; Ono, N.

doi:10.1002/chin.199439156

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“…Target compounds 812 were released by pyrrole annulation via the reaction of the vinyl sulfone moiety with alkyl isocyanoacetates. The mechanism of the pyrrole cyclization via the reaction of isocyanoacetates with electrondeficient alkenes was described by Barton and Zard 255 for nitroalkenes and by Uno et al 256 for vinyl sulfones. The basecatalyzed Michael addition of isocyanoacetate to a vinyl sulfone was followed by the cyclization of the Michael adduct anion onto the isocyano group.…”

Section: Cleavage By C-nucleophilesmentioning

confidence: 99%

Traceless Solid-Phase Organic Synthesis

2019

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Traceless solid-phase synthesis represents an ultimate sophisticated synthetic strategy on insoluble supports. Compounds synthesized on solid supports can be released without a trace of the linker that was used to tether the intermediates during the synthesis. Thus, the target products are composed only of the components (atoms, functional groups) inherent to the target core structure. A wide variety of synthetic strategies have been developed to prepare products in a traceless manner, and this review is dedicated to all aspects of traceless solid-phase organic synthesis. Importantly, the synthesis does not need to be carried out on a linker designed for traceless synthesis; most of the synthetic approaches described herein were developed using standard, commercially available linkers (originally devised for solid-phase peptide synthesis). The type of structure prepared in a traceless fashion is not restricted. The individual synthetic approaches are divided into eight sections, each devoted to a different methodology for traceless synthesis. Each section consists of a brief outline of the synthetic strategy followed by a description of individual reported syntheses.

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Section: Cleavage By C-nucleophilesmentioning

confidence: 99%