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Palladium-catalyzed regio- and stereoselective ?-arylation of tertiary allylic amines: identification of potent adenylyl cyclase inhibitors.


ABSTRACT: Substituted allylic amines and their derivatives are key structural motifs of many drug molecules and natural products. A general, mild, and practical palladium-catalyzed ?-arylation of tertiary allylic amines, one of the most challenging Heck arylation substrates, has been developed. The ?-arylation products were obtained in excellent regio- and stereoselectivity. Moreover, novel and potent adenylyl cyclase inhibitors with the potential for treating neuropathic and inflammatory pain have been identified from the ?-arylation products.

SUBMITTER: Ye Z 

PROVIDER: S-EPMC4692243 | biostudies-literature | 2015 Feb

REPOSITORIES: biostudies-literature

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Palladium-catalyzed regio- and stereoselective γ-arylation of tertiary allylic amines: identification of potent adenylyl cyclase inhibitors.

Ye Zhishi Z   Brust Tarsis F TF   Watts Val J VJ   Dai Mingji M  

Organic letters 20150210 4


Substituted allylic amines and their derivatives are key structural motifs of many drug molecules and natural products. A general, mild, and practical palladium-catalyzed γ-arylation of tertiary allylic amines, one of the most challenging Heck arylation substrates, has been developed. The γ-arylation products were obtained in excellent regio- and stereoselectivity. Moreover, novel and potent adenylyl cyclase inhibitors with the potential for treating neuropathic and inflammatory pain have been i  ...[more]

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