jo5010247_si_001.cif (465.7 kB)

Palladium/ClickFerrophos-Catalyzed Asymmetric Domino Allylstannylation–Heck Reaction of o‑Formylaryl Triflate

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posted on 05.09.2014, 00:00 by Atsuo Tada, Yuichiro Tokoro, Shin-ichi Fukuzawa
Asymmetric domino allylstannylation–Heck reaction of o-formylaryl triflates was successively catalyzed by Pd/ClickFerrophos to give the 3-methylene-indan-1-ols in good yields with good to excellent enantioselectivities. The benefit of the reaction is that the starting o-formylaryl triflates are prepared from easily accessible salicylaldehyde derivatives, and the variation of the product, chiral 3-methylene-indan-1-ols, can be expanded. The reaction with 4-substituted substrates gave the corresponding 3-methylene-indan-1-ols in good yields with high enantioselectivities, whereas the reaction with 5- and 6-substituted substrates occasionally afforded the corresponding Stille coupling product in significant amounts along with the desired 3-methylene-indan-1-ols.