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Palladium-Catalyzed Asymmetric Allylic Alkylations with Toluene Derivatives as Pronucleophiles.

ABSTRACT: 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 ?-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.

SUBMITTER: Mao J

PROVIDER: S-EPMC4836847 | biostudies-literature | 2016 Feb

REPOSITORIES: biostudies-literature

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Palladium-Catalyzed Asymmetric Allylic Alkylations with Toluene Derivatives as Pronucleophiles.

Mao Jianyou J Zhang Jiadi J Jiang Hui H Bellomo Ana A Zhang Mengnan M Gao Zidong Z Dreher Spencer D SD Walsh Patrick J PJ

Angewandte Chemie (International ed. in English) 20160112 7

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 ...[more]

PMID: 26756125

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