An Ion-Pair Immobilization Strategy in Rhodium-Catalyzed Asymmetric Transfer Hydrogenation
General Procedure for Asymmetric Transfer
Hydrogenation of Aromatic Ketones
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A typical procedure was as follows: The catalyst 1 (3.0 mg,
4
.00 mmol), HCO Na (0.68 g, 10.0 mmol), Bu NBr (0.29 g,
2
4
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0.80 mmol), ketone (2.0 mmol) and 4.0 mL water were
added in a 10-mL round-bottom flask in turn. The flask was
immediately sealed with a rubber septum and the mixture
sonicated by immersion in an ultrasonic cleaning bath
(
SONICS (USA) VCX750, 50 kHz, 150 W). During that
time, the reaction was monitored constantly by TLC. After
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centrifuge (10000 r/min) for the recycle experiment. The
2
719.
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2
aqueous solution was extracted by Et O (3ꢂ3.0 mL). The
2
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combined Et O was washed with brine twice and dehydrat-
2
[
ed with Na SO . After the evaporation of Et O, the residue
2
4
2
was purified by silica gel flash column chromatography to
afford the desired product. The conversion and the ee value
could be determined by chiral GC using a Supelco b-Dex
2
007, 46, 6861; b) S. Y. Bai, H. Q. Yang, P. Wang, J. S.
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4
120 chiral column (30 mꢂ0.25 mm AHCNUTGTERNNUN(G i.d.), 0.25 mm film) or
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a HPLC analysis with a UV-Vis detector using a Daicel OJ-
H chiralcel columns (F 0.46ꢂ25 cm).
[
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Acknowledgements
We are grateful to China National Natural Science Founda-
tion (20673072), Shanghai Sciences and Technologies Devel-
opment Fund (10J1400103, 10JC1412300 and 12nm0500500)
and Shanghai Municipal Education Commission (No.
1
2ZZ135, S30406) for financial support.
2
003, 86, 1753.
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