TY - JOUR
T1 - Catalytic, nucleophilic allylation of aldehydes with 2-substituted allylic acetates
T2 - Carbon-carbon bond formation driven by the water-gas shift reaction
AU - Denmark, Scott E.
AU - Matesich, Zachery D.
PY - 2014/7/3
Y1 - 2014/7/3
N2 - The ruthenium-catalyzed allylation of aldehydes with allylic acetates has been expanded to incorporate substituents at the 2-position of the allylic components. Allylic acetates bearing a variety of substituents (CO 2-t-Bu, COMe, Ph, CH(OEt)2, and Me) undergo high-yielding additions with aromatic, α,β-unsaturated, and aliphatic aldehydes. The conditions of the reaction were found to be mild (75°C, 24-48 h) and only required the use of 2-3 mol % of the triruthenium dodecacarbonyl catalyst under 40-80 psi of CO. The stoichiometries of water and allylic acetate employed were found to be critical to reaction efficiency.
AB - The ruthenium-catalyzed allylation of aldehydes with allylic acetates has been expanded to incorporate substituents at the 2-position of the allylic components. Allylic acetates bearing a variety of substituents (CO 2-t-Bu, COMe, Ph, CH(OEt)2, and Me) undergo high-yielding additions with aromatic, α,β-unsaturated, and aliphatic aldehydes. The conditions of the reaction were found to be mild (75°C, 24-48 h) and only required the use of 2-3 mol % of the triruthenium dodecacarbonyl catalyst under 40-80 psi of CO. The stoichiometries of water and allylic acetate employed were found to be critical to reaction efficiency.
UR - http://www.scopus.com/inward/record.url?scp=84903714685&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84903714685&partnerID=8YFLogxK
U2 - 10.1021/jo501004j
DO - 10.1021/jo501004j
M3 - Article
C2 - 24927196
AN - SCOPUS:84903714685
SN - 0022-3263
VL - 79
SP - 5970
EP - 5986
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 13
ER -