Unknown

Dataset Information

0

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


ABSTRACT: 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.

SUBMITTER: Zielke K 

PROVIDER: S-EPMC6618147 | biostudies-literature | 2019 Jun

REPOSITORIES: biostudies-literature

altmetric image

Publications

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

Zielke Katharina K   Kováč Ondřej O   Winter Michael M   Pospíšil Jiří J   Waser Mario M  

Chemistry (Weinheim an der Bergstrasse, Germany) 20190521 34


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. ...[more]

Similar Datasets

| S-EPMC5420312 | biostudies-literature
| S-EPMC4270411 | biostudies-literature
| S-EPMC5799871 | biostudies-literature
| S-EPMC2888001 | biostudies-literature
| S-EPMC5716626 | biostudies-other
| S-EPMC8588318 | biostudies-literature
| S-EPMC10763553 | biostudies-literature
| S-EPMC7155103 | biostudies-literature
| S-EPMC4500648 | biostudies-literature
| S-EPMC8587149 | biostudies-literature