2017
DOI: 10.1021/acs.joc.7b02287
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One-Pot Asymmetric Synthesis of Alkylidene 1-Alkylindan-1-ols Using Brønsted Acid and Palladium Catalysis

Abstract: 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 … Show more

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Cited by 5 publications
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“…The authors further extended this cascade reaction to the asymmetric synthesis of 3-methyleneindanes 383 bearing a tertiary alcohol center, employing ( S )-3,3′-Br 2 -BINOL as a chiral Brønsted acid and 2-bromoaryl ketones 381 as substrates (Scheme 84). 174 Of note, both chiral indanols 383 and their endo -alkene isomers 384 were obtained in this transformation.…”
Section: Cyclization Based On Heck Reactionmentioning
confidence: 91%
“…The authors further extended this cascade reaction to the asymmetric synthesis of 3-methyleneindanes 383 bearing a tertiary alcohol center, employing ( S )-3,3′-Br 2 -BINOL as a chiral Brønsted acid and 2-bromoaryl ketones 381 as substrates (Scheme 84). 174 Of note, both chiral indanols 383 and their endo -alkene isomers 384 were obtained in this transformation.…”
Section: Cyclization Based On Heck Reactionmentioning
confidence: 91%