TY - JOUR
T1 - Tandem catalytic triple-bond cleavage of alkyne in association with aldehyde, alkene, and water
AU - Cha, Kyung Mi
AU - Jo, Eun Ae
AU - Jun, Chul Ho
PY - 2009
Y1 - 2009
N2 - In this tandem reaction the carbon-carbon triple bond of an alkyne is catalytically cleaved in association with aldehyde, al-kene, and H2O under catalyst mixtures of Rh(I), 2-amino-3-picoline, primary amine, and acid. The reaction starts with chelation-assisted hydroacylation of the alkyne with an aldehyde. The retro-Mannich-type fragmentation of the resulting ,α,β-unsaturated ketimine by an amine and acid affords a ketimine and an aldimine, which is trapped by an alkene and give ketones after hydrolysis.
AB - In this tandem reaction the carbon-carbon triple bond of an alkyne is catalytically cleaved in association with aldehyde, al-kene, and H2O under catalyst mixtures of Rh(I), 2-amino-3-picoline, primary amine, and acid. The reaction starts with chelation-assisted hydroacylation of the alkyne with an aldehyde. The retro-Mannich-type fragmentation of the resulting ,α,β-unsaturated ketimine by an amine and acid affords a ketimine and an aldimine, which is trapped by an alkene and give ketones after hydrolysis.
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U2 - 10.1055/s-0029-1218000
DO - 10.1055/s-0029-1218000
M3 - Article
AN - SCOPUS:72049089570
SN - 0936-5214
SP - 2939
EP - 2942
JO - Synlett
JF - Synlett
IS - 18
ER -