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Enantioselective Palladium‐Catalyzed Carbonylative Carbocyclization of Enallenes via Cross‐Dehydrogenative Coupling with Terminal Alkynes: Efficient Construction of α‐Chirality of Ketones
Author(s) -
Yang Bin,
Qiu Youai,
Jiang Tuo,
Wulff William D.,
Yin Xiaopeng,
Zhu Can,
Bäckvall JanE.
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201612385
Subject(s) - enantioselective synthesis , alkyne , catalysis , phosphoric acid , palladium , chemistry , chirality (physics) , brønsted–lowry acid–base theory , combinatorial chemistry , enantiomer , organic chemistry , enantiomeric excess , physics , chiral anomaly , quantum mechanics , nambu–jona lasinio model , fermion
An enantioselective Pd II /Brønsted acid‐catalyzed carbonylative carbocyclization of enallenes ending with a cross‐dehydrogenative coupling (CDC) with a terminal alkyne was developed. VAPOL phosphoric acid was found as the best co‐catalyst among the examined 28 chiral acids, for inducing the enantioselectivity of α‐chiral ketones. As a result, a number of chiral cyclopentenones were easily synthesized in good to excellent enantiomeric ratio with good yields.