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Direct Regio- and Diastereoselective Synthesis of δ-Lactams from Acrylamides and Unactivated Alkenes Initiated by RhIII-Catalyzed C-H Activation
被引:36
|作者:
Lee, Sumin
[1
]
Semakul, Natthawat
[1
]
Rovis, Tomislav
[1
]
机构:
[1] Columbia Univ, Dept Chem, New York, NY 10027 USA
关键词:
alkene functionalization;
C-H activation;
piperidines;
Rhodium;
delta-lactams;
BOND;
REACTIVITY;
BENZAMIDES;
ALKYNES;
ACCESS;
D O I:
10.1002/anie.201916332
中图分类号:
O6 [化学];
学科分类号:
0703 ;
摘要:
We report a Rh-III-catalyzed regio- and diastereoselective synthesis of delta-lactams from readily available acrylamide derivatives and unactivated alkenes. The reaction provides a rapid route to a diverse set of delta-lactams in good yield and stereoselectivity, which serve as useful building blocks for substituted piperidines. The regioselectivity of the reaction with unactivated terminal alkene is significantly improved by using Cp-t ligand on the Rh-III catalyst. The synthetic utility of the reaction is demonstrated by the preparation of a potential drug candidate containing a trisubstituted piperidine moiety. Mechanistic studies show that the reversibility of the C-H activation depends on the choice of Cp ligand on the Rh-III catalyst. The irreversible C-H activation is observed and becomes turnover-limiting with [(CpRhCl2)-Rh-t](2) as catalyst.
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页码:4965 / 4969
页数:5
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