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Enantioselective Catalytic [4+1]‐Cyclization of ortho ‐Hydroxy‐ para ‐Quinone Methides with Allenoates
Author(s) -
Zielke Katharina,
Kováč Ondřej,
Winter Michael,
Pospíšil Jiří,
Waser Mario
Publication year - 2019
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.201901784
Subject(s) - enantioselective synthesis , diastereomer , phosphine , quinone , annulation , catalysis , enantiomer , chemistry , organic chemistry , enantiomeric excess , combinatorial chemistry , medicinal chemistry
The first highly asymmetric catalytic synthesis of densely functionalized dihydrobenzofurans is reported, which starts from ortho ‐hydroxy‐containing para ‐quinone methides. The reaction relies on an unprecedented formal [4+1]‐annulation of these quinone methides with allenoates in the presence of a commercially available chiral phosphine catalyst. The chiral dihydrobenzofurans were obtained as single diastereomers in yields up to 90 % and with enantiomeric ratios up to 95:5.