Palladium-Catalyzed Carbo-Oxygenation of Propargylic Amines using in Situ Tether Formation

1,2-Amino alcohols and -aminocarbonyls are frequently found in natural products, drugs, chiral auxiliaries, and catalysts. This work reports a new method for the palladium-catalyzed oxyalkynylation and oxyarylation of propargylic amines. The reaction is perfectly regioselective based on the in situ introduction of a hemiacetal tether derived from trifluoroacetaldehyde. cis-Selective carbo-oxygenation was achieved for terminal alkynes, whereas internal alkynes gave trans-carbo-oxygenation products. The obtained enol ethers could be easily transformed into 1,2-amino alcohols or -amino ketones using hydrogenation or hydrolysis, respectively.


Published in:
Chemistry-A European Journal, 25, 12, 3010-3013
Year:
Feb 26 2019
ISSN:
0947-6539
1521-3765
Keywords:
Laboratories:


Note: The file is under embargo until: 2020-01-08


 Record created 2019-06-18, last modified 2019-08-12

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