z-logo
Premium
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.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here
Accelerating Research

Address

John Eccles House
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom