Feng Lang et al.
COMMUNICATIONS
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Figure 2. Stereochemical pathway for the asymmetric 1,4-ad-
dition.
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Procedure for the 1,4-Addition
Under an argon atmosphere and at room temperature, to a
10-mL Schlenk tube with a teflon cap was added ligand 1e
(5.1 mg. 2.4 mol%) and [RhACHTNUTGRNE(UNG C2H4)2Cl]2 (1.9 mg, 1.0 mol%)
followed by 1.0 mL toluene. The mixture was stirred for half
hour and arylboronic acid (1.0 mmol) was added. The tem-
perature was increased to 408C and enone (0.5 mmol) was
then added via syringe followed by degassed KOH (2.5M in
H2O, 1.0 mL, 0.25 mmol). The reaction mixture was stirred
at 408C for half hour (monitored by TLC). The reaction
mixture was then directly charged onto a column (silica gel)
for flash chromatography with a mixture of petroleum
ether/EtOAc to afford the product.
Acknowledgements
We are grateful to the support of NSFC (No. 20872139), the
West Light Foundation of Chinese Academy of Sciences and
973 program (2010CB833301).
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Adv. Synth. Catal. 2010, 352, 843 – 846