Pd II-Catalyzed stereospecific formation of tetrahydro- and 3,6-dihydro[2 H]pyran rings: 1,3-chirality transfer by intramolecular oxypalladation reaction

[Display omitted] The stereospecific synthesis of 2,6-disubstituted tetrahydropyran and 3,6-dihydro[2 H]pyran is described. The Pd II-catalyzed cyclization of the hydroxy nucleophile to the allylic alcohol takes place efficiently under mild conditions, with the stereogenic center on the secondary al...

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Bibliographic Details
Published inTetrahedron: asymmetry Vol. 16; no. 7; pp. 1299 - 1303
Main Authors Uenishi, Jun’ichi, Ohmi, Masashi, Ueda, Atsushi
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 04.04.2005
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
LEUCASCANDROLIDE-A
LASONOLIDE
ORGANIC-SOLVENTS
TETRAHYDROPYRANS
CYTOTOXIC MACROLIDE
STEREOSELECTIVE-SYNTHESIS
GLIDING BACTERIA
METABOLITE
CYCLIZATION
MARINE SPONGE
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Summary:[Display omitted] The stereospecific synthesis of 2,6-disubstituted tetrahydropyran and 3,6-dihydro[2 H]pyran is described. The Pd II-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-S N2′ type process.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2005.02.006