Synthesis p. 433 - 435 (1992)
Update date:2022-08-17
Topics:
Bringmann
Hartung
The atropo-enantioselective preparation of the chiral biaryl 2-hydroxymethyl-1-(2-hydroxy-4,6-dimethoxyphenyl)naphthalene (7) from 1,3-dimethoxy-6H-benzo[b]naphtho[1,2-d]pyran-6-one (3) is described, whereby two formal problems of stereoselective biaryl synthesis are independently solved: The carbon-carbon bond formation by the intramolecular aryl coupling of the ester-type prefixed aromatic halves, and the asymmetric induction at the pre-formed biaryl axis by the subsequent stereoselective ring-opening reaction, using chiral hydrogen nucleophiles.
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Doi:10.1021/jacs.7b10796
(2018)Doi:10.1016/0040-4020(78)88154-X
(1978)Doi:10.1021/om00037a066
(1992)Doi:10.1021/jo00221a021
(1985)Doi:10.1107/S0108270110027678
(2010)Doi:10.1016/j.mcat.2019.110570
(2020)