3 years ago

One-Pot Asymmetric Synthesis of Alkylidene 1-Alkylindan-1-ols Using Brønsted Acid and Palladium Catalysis

One-Pot Asymmetric Synthesis of Alkylidene 1-Alkylindan-1-ols Using Brønsted Acid and Palladium Catalysis
Réka J. Faggyas, Ewen D. D. Calder, Claire Wilson, Andrew Sutherland
A one-pot catalytic enantioselective allylboration/Mizoroki–Heck reaction of 2-bromoaryl ketones has been developed for the asymmetric synthesis of 3-methyleneindanes bearing a tertiary alcohol center. Brønsted acid-catalyzed allylboration with a chiral BINOL derivative was followed by a palladium-catalyzed Mizoroki–Heck cyclization, resulting in selective formation of the exo-alkene. This novel protocol provides a concise and scalable approach to 1-alkyl-3-methyleneindan-1-ols in high enantiomeric ratios (up to 96:4 er). The potential of these compounds as chiral building blocks was demonstrated with efficient transformation to optically active diol and amino alcohol scaffolds.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b02287

DOI: 10.1021/acs.joc.7b02287

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