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Reiterative Synthesis of trans ‐Fused Polytetrahydropyrans Using the Oxiranyl Anion
Author(s) -
Mori Yuji
Publication year - 1997
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.19970030604
Subject(s) - tetrahydropyran , nucleophile , trifluoromethanesulfonate , epoxide , chemistry , alkylation , bicyclic molecule , ion , methanol , stereochemistry , ring (chemistry) , medicinal chemistry , combinatorial chemistry , catalysis , organic chemistry
The oxiranyl anion is a very unstable nucleophilic epoxide. This previously uncommon nucleophile has now been used for the synthesis of polycyclic ethers. Alkylation of an oxiranyl anion, a three‐carbon building block, with a triflate derived from tetrahydropyran‐methanol followed by acid‐catalyzed 6‐ endo cyclization provides a trans ‐fused bicyclic compound. Reiterative application of this procedure enables the rapid construction of trans ‐fused polytetrahydropyrans.