期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 25, 期 34, 页码 8163-8168出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201901784
关键词
allenoates; annulation; diastereoselectivity; enantioselectivity; organocatalysis
资金
- Austrian Science Funds (FWF) [P26387-N28]
- European Union through the EFRE INTERREG IV ETC-AT-CZ program [M00146]
- Internal Grant Agency of Palacky University [IGA_PrF_2019_027]
- European Regional Development Fund Project Centre for Experimental Plant Biology [CZ.02.1.01/0.0/0.0/16_019/0000738]
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.
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