Enantioselective Catalytic [4+1]-Cyclization of ortho-Hydroxy-para-Quinone Methides with Allenoates

0507810 - ÚEB 2020 RIV DE eng J - Journal Article
Zielke, K. - Kováč, O. - Winter, M. - Pospíšil, Jiří - Waser, M.
Enantioselective Catalytic [4+1]-Cyclization of ortho-Hydroxy-para-Quinone Methides with Allenoates.
Chemistry - A European Journal. Roč. 25, č. 34 (2019), s. 8163-8168. ISSN 0947-6539. E-ISSN 1521-3765
R&D Projects: GA MŠMT(CZ) EF16_019/0000738
Institutional support: RVO:61389030
Keywords : allenoates * annulation * diastereoselectivity * enantioselectivity * organocatalysis
OECD category: Biochemical research methods
Impact factor: 4.857, year: 2019
Method of publishing: Open access
http://dx.doi.org/10.1002/chem.201901784

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.
Permanent Link: http://hdl.handle.net/11104/0298778