PdII-Catalyzed stereospecific formation of tetrahydro- and 3,6-dihydro[2H]pyran rings: 1,3-chirality transfer by intramolecular oxypalladation reaction |
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| Institution: | 1. Department of Chemistry, Section for Chemical Biology and Nanobioscience, Faculty of Science, University of Copenhagen, Thorvaldsensvej 40, 1871 Frederiksberg C, Denmark;2. Department of Drug Design and Pharmacology, Faculty of Health and Medical Sciences, University of Copenhagen, Denmark;3. CNRS, UMR 6296, ICCF, BP 80026, 63171 Aubière, France;4. Clermont Université, Université Blaise Pascal, Institut de Chimie de Clermont-Ferrand, BP 10448, 63000 Clermont-Ferrand, France;1. Department of Biochemistry and Medical Chemistry, University of Pécs, Medical School, Szigeti u. 12, H-7624 Pécs, Hungary;2. Department of Pharmacognosy, University of Pécs, Medical School, Rókus u. 2, H-7624 Pécs, Hungary;1. Chemical Biology Unit, Division of Organic Chemistry, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411008, India;2. CSIR-Institute of Genomics and Integrative Biology, Mall Road, New Delhi 110007, India;1. College of Chemistry and Materials, South-Central University for Nationalities, Wuhan, China;2. College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, China;1. Istituto di Struttura della Materia ISM-CNR, Via Fosso del Cavaliere 100, 00133 Roma, Italy;2. Center of Materials Technology & Photonics Technological Educational Institute (TEI) of Crete and, Electrical Engineering Department TEI of Crete, Heraklion, 71004 Crete, Greece;3. European Synchrotron Radiation Facility, 6 Jules Horowitz, 38000 Grenoble, France;4. Institute of Electronic Structure and Laser (IESL), Foundation for Research and Technology Hellas (FORTH), & Dept. of Materials Science and Technology, Univ. of Crete, Heraklion, Crete, Greece;1. Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, Sector 10, Jankipuram Extension, Sitapur Road, Lucknow 226031, India;2. Molecular & Structural Biology Division, CSIR-Central Drug Research Institute, Sector 10, Jankipuram Extension, Sitapur Road, Lucknow 226031, India;3. Academy of Scientific and Innovative Research, New Delhi, India |
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| Abstract: | The stereospecific synthesis of 2,6-disubstituted tetrahydropyran and 3,6-dihydro2H]pyran is described. The PdII-catalyzed cyclization of the hydroxy nucleophile to the allylic alcohol takes place efficiently under mild conditions, with the stereogenic center on the secondary allylic alcohol transfers to a newly generated stereogenic center on pyran ring via a syn-SN2′ type process. |
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