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Diastereoselective Synthesis of trans ‐2,3‐Diaryl(heteroaryl)‐3,6‐dihydropyrans by an Allylboration/Ring‐Closing‐Metathesis Sequence
Author(s) -
Nocquet PierreAntoine,
Corbu Andrei,
Meerpoel Lieven,
Stansfield Ian,
Berthelot Didier,
Angibaud Patrick,
Cossy Janine
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700448
Subject(s) - chemistry , dihydropyran , ring closing metathesis , metathesis , allylic rearrangement , stereochemistry , sequence (biology) , ring (chemistry) , organic chemistry , catalysis , biochemistry , polymer , polymerization
trans ‐2,3‐Diaryl(heteroaryl)‐dihydropyrans were synthesized by an allylboration/ring‐closing‐metathesis sequence, using allylboranes formed in situ from the corresponding allylic alcohols. Aryl(heteroaryl) substituents were thus installed diastereoselectively onto dihydropyran rings in a trans fashion. These disubstituted dihydropyrans were further transformed into monosaccharide‐like tetrahydropyrans.