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Palladium‐Catalyzed Asymmetric Allylic Alkylations with Toluene Derivatives as Pronucleophiles
Author(s) -
Mao Jianyou,
Zhang Jiadi,
Jiang Hui,
Bellomo Ana,
Zhang Mengnan,
Gao Zidong,
Dreher Spencer D.,
Walsh Patrick J.
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201509917
Subject(s) - enantioselective synthesis , allylic rearrangement , palladium , chemistry , nucleophile , electrophile , catalysis , toluene , combinatorial chemistry , organic chemistry , tsuji–trost reaction
The first two highly enantioselective palladium‐catalyzed allylic alkylations with benzylic nucleophiles, activated with Cr(CO) 3 , have been developed. These methods enable the enantioselective synthesis of α‐2‐propenyl benzyl motifs, which are important scaffolds in natural products and pharmaceuticals. A variety of cyclic and acyclic allylic carbonates are competent electrophilic partners furnishing the products in excellent enantioselectivity (up to 99 % ee and 92 % yield). This approach was employed to prepare a nonsteroidal anti‐inflammatory drug analogue.