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Site-Selective Modification of a Porpholactone-Selective Synthesis of 12,13- and 17,18-Dihydroporpholactones.

ABSTRACT: The reaction of meso-tetrakis(pentafluorophenyl)porpholactone with azomethine ylides and nitrones affords pyrrolidine-fused and isoxazolidine-fused dihydroporpholactones that display, respectively, isobacteriochlorin- and chlorin-type UV-Vis spectra. These reactions are site-selective, yielding, respectively, 17,18- or 12,13-dihydroporpholactones. The crystal and molecular features of pyrrolidine-fused and isoxazolidine-fused dihydroporpholactones were unveiled from single-crystal X-ray diffraction studies.

SUBMITTER: Cerqueira AFR

PROVIDER: S-EPMC7321334 | biostudies-literature | 2020 Jun

REPOSITORIES: biostudies-literature

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Site-Selective Modification of a Porpholactone-Selective Synthesis of 12,13- and 17,18-Dihydroporpholactones.

Cerqueira Ana F R AFR Snarskis Gustautas G Zurauskas Jonas J Guieu Samuel S Paz Filipe A Almeida FAA Tomé Augusto C AC

Molecules (Basel, Switzerland) 20200606 11

The reaction of <i>meso</i>-tetrakis(pentafluorophenyl)porpholactone with azomethine ylides and nitrones affords pyrrolidine-fused and isoxazolidine-fused dihydroporpholactones that display, respectively, isobacteriochlorin- and chlorin-type UV-Vis spectra. These reactions are site-selective, yielding, respectively, 17,18- or 12,13-dihydroporpholactones. The crystal and molecular features of pyrrolidine-fused and isoxazolidine-fused dihydroporpholactones were unveiled from single-crystal X-ray d ...[more]

PMID: 32517216

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