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Organic Letters

Volumn 9, Issue 9, 2007, Pages 1651-1654

Intermolecular asymmetric reductive aldol reaction of ketones as acceptors promoted by chiral Rh(Phebox) catalyst

(2) Shiomi, Takushi a Nishiyama, Hisao a

a NAGOYA UNIVERSITY (Japan)

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EID: 34248360397 PISSN: 15237060 EISSN: None Source Type: Journal
DOI: 10.1021/ol070251d Document Type: Article

Times cited : (71)

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42
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- Typical procedure: Table 1, entry 7: the rhodium complex, Rh-(Phebox-ip)(OAc)2(H2O, 5.4 mg, 0.01 mmol, was placed in a 10 mL flask. Under an argon atmosphere, ethyl cinnamate (176 mg, 1.0 mmol) and acetone (0.20 mL) were added. Methyldiphenylsilane (258 mg, 1.3 mmol) was slowly added at 50°C by syringe, and the mixture was stirred for 0.5 h. The reaction was monitored by TLC examination; Rf ca. 0.8 for the silyl ether of the aldol product (eluent: EtOAc/hexane, 1:2, To the mixture was added EtOH (1 mL) and aq HCl (1 mL, 4 N) at 0°C, then the mixture was stirred at room temperature for 4 h; TLC, Rf ca. 0.4 for the aldol product 2 (eluent: EtOAc/hexane, 1:2, The mixture was treated with aq NaHCO3 (ca. 15 mL) and extracted with EtOAc (3 × 5 mL, The combined organic layer was washed with saturated brine 5 mL, then dried over Na2SO4. After concentration, the residue was purified by silica gel
- 3). Chromatography: DAICEL CHIRALPAK AS-H; eluent: hexane/2-propanol (99:1) (0.5 mL/min); retention time: 22.3 min (minor), 26.3 min (major); 97% ee. Determination of absolute configuration, see the Supporting Information.

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