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Highly Regio- and Stereoselective Catalytic Synthesis of Conjugated Dienes and Polyenes.

ABSTRACT: Conjugated dienes and polyenes are typically synthesized by sequential introduction of C?C bonds. Here, we report a practical and scalable, catalytic dienylation that is highly regio- and stereoselective for both C?C bonds. The reaction is enabled by a stereoselective palladium-catalyzed cross-coupling that is preceded by a regioselective base-induced ring opening of readily available sulfolenes. The dienylation reaction is particularly useful for the synthesis of synthetically challenging dienes containing cis double bonds. We also show that the reaction can serve as a synthetic platform for the construction of conjugated polyenes.

SUBMITTER: Nguyen VT

PROVIDER: S-EPMC6171353 | biostudies-literature | 2018 Jul

REPOSITORIES: biostudies-literature

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Highly Regio- and Stereoselective Catalytic Synthesis of Conjugated Dienes and Polyenes.

Nguyen Vu T VT Dang Hang T HT Pham Hoang H HH Nguyen Viet D VD Flores-Hansen Carsten C Arman Hadi D HD Larionov Oleg V OV

Journal of the American Chemical Society 20180626 27

Conjugated dienes and polyenes are typically synthesized by sequential introduction of C═C bonds. Here, we report a practical and scalable, catalytic dienylation that is highly regio- and stereoselective for both C═C bonds. The reaction is enabled by a stereoselective palladium-catalyzed cross-coupling that is preceded by a regioselective base-induced ring opening of readily available sulfolenes. The dienylation reaction is particularly useful for the synthesis of synthetically challenging diene ...[more]

PMID: 29936839

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