Categories: C=C Bond Formation >
Synthesis of allenes
| Related: |  |
 |
Recent Literature
Various propargylic amines underwent a palladium-catalyzed hydrogen-transfer
reaction in the presence of (C6F5)3P,
giving the corresponding allenes in good yields.
H. Nakamura, T. Kamakura, M. Ishikura, J.-F. Biellmann, J. Am. Chem. Soc.,
2004, 126, 5958-5959.
1,1-diarylpropadienes and
1,3-diarylpropynes can be prepared by the sequential lithiation of
1-aryl-1-propynes, transmetalation, and the corresponding Pd(0)-catalyzed
cross-coupling with aryl halides.
S. Ma, Q. He, X. Zhang, J. Org. Chem., 2005, 70, 3336-3338.
Homoallenic alcohols are prepared from various propargyl vinyl ethers using a
trinuclear gold(I)-oxo complex, [(Ph3PAu)3O]BF4,
as a catalyst for propargyl Claisen rearrangement at room temperature.
B. D. Sherry, F. D. Toste, J. Am. Chem. Soc.,
2004, 126, 15978-15979.
Enantioenriched propargyl mesylates or perfluorobenzoates react with α-(N-carbamoyl)alkylcuprates
to afford scalemic α-(N-carbamoyl) allenes. Subsequent N-Boc
deprotection and AgNO3-promoted cyclization afford enantioenriched
N-alkyl-3-pyrrolines.
R. K. Dieter, N. Chen, V. K. Gore, J. Org. Chem., 2006, 71, 8755-8760.
