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A Multiple Five‐Membered‐Ring‐Selective Williamson Reaction as a Key Step in the Stereoselective Construction of 2,5‐Linked Oligo(tetrahydrofuran)s
Author(s) -
Wagner Holger,
Koert Ulrich
Publication year - 1994
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199418731
Subject(s) - tetrahydrofuran , reagent , stereoselectivity , ring (chemistry) , key (lock) , chemistry , sequence (biology) , combinatorial chemistry , organic chemistry , computer science , catalysis , computer security , biochemistry , solvent
Four tetrahydrofuran rings in one step can be constructed with the multiple five‐mem‐bered‐ring‐selective Williamson reaction ( 1 → 2 ). The tetratosylate 1 is obtained from the corresponding dialkyne by a reagent‐controlled, diastereoselective dihy‐droxylation. This reaction sequence opens up an efficient route to enantiomerically pure oligo(tetrahydrofuran)s.