Pd(0)-Catalyzed Alkene Oxy- and Aminoalkynylation with Aliphatic Bromoacetylenes

Tetrahydrofurans and pyrrolidines are among the most important heterocycles found in bioactive compounds. Cyclization-functionalization domino reactions of alcohols or amines onto olefins,constitute one of the most efficient methods to access them. In this context oxy- and aminoalkynylation are especially important reactions because of the numerous transformations possible with the triple bond of acetylenes yet these methods have been limited to the use of silyl protected acetylenes. Herein we report the first palladium-catalyzed oxy- and aminoalkynylation using aliphatic bromoalkynes which proceeded with high diastereoselectivity and functional group tolerance. A one-pot hydrogenation of the triple bond gave then access to alkyl-substituted tetrahydrofurans and pyrroldines. Finally a detailed study of the side products formed during the reaction gave a first insight into the reaction mechanism.


Published in:
Journal Of Organic Chemistry, 78, 8, 3783-3801
Year:
2013
Publisher:
Washington, American Chemical Society
ISSN:
0022-3263
Laboratories:




 Record created 2013-10-01, last modified 2018-03-17

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