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Palladium‐Catalyzed Carbo‐Oxygenation of Propargylic Amines using in Situ Tether Formation
Author(s) -
Greenwood Phillip D. G.,
Grenet Erwann,
Waser Jerome
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201900020
Subject(s) - palladium , catalysis , regioselectivity , chemistry , hemiacetal , hydrolysis , in situ , enol , organic chemistry , oxygenation , combinatorial chemistry , ecology , biology
Abstract 1,2‐Amino alcohols and α‐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 α‐amino ketones using hydrogenation or hydrolysis, respectively.