COMMUNICATIONS
Palladium-Catalyzed Three-Component Reaction
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catalyst system, which provides facile access into (E)-
anti-homoallylic alcohols. The present method not
only allows the introduction of n-alkyl, sec-alkyl, and
aryl groups into the alkene of the homoallylic alco-
hols but also gives access to effective control of the
(E)-geometry at the double bond. Interestingly, the
present reaction proceeds through a s-allylpalladium-
controlled cyclic transition state. Further investiga-
tions along these lines are currently underway in our
laboratories.
Experimental Section
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Typical Procedure for Palladium-Catalyzed Three-
Component Reaction; Synthesis of 4a
A 10-mL two-neck round-bottom flask was charged with
Pd2(dba)3CHCl3 (12.9 mg, 0.0125 mmol), Xantphos (14.5 mg,
0.025 mmol), and toluene (1 mL). The mixture was stirred at
room temperature for 0.5 h. A solution of 1a (232.6 mg,
0.5 mmol) and benzaldehyde (2a) (123 mL, 1.2 mmol) in tol-
uene (1 mL) and Et3B (3a) (1.2 mmol, 1.0M hexane solu-
tion) were then successively added. The reaction mixture
was stirred at 508C for 0.5 h. Upon completion of the reac-
tion, the reaction mixture was diluted with EtOAc (20 mL)
and washed with saturated NH4Cl (220 mL) and brine (2
20 mL). The combined organic layers were dried over
MgSO4 and concentrated. The residue was purified by silica
gel chromatography (Rf 0.45, EtOAc/hexane=1/4) to give
4a as a yellow oil; yield: 97.2 mg (77%).
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[10] See the Supporting Information for details.
[11] CCDC 1419321 contains the supplementary crystallo-
graphic data for this paper. These data can be obtained
free of charge from The Cambridge Crystallographic
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Acknowledgements
We thank Prof. Ryuta Miyatake (University of Toyama) for
his assistance in X-ray crystallographic analysis. This work
was financially supported by the JSPS KAKENHI Grant
Number 15K05496.
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Adv. Synth. Catal. 2016, 358, 1023 – 1028
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