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Organic Letters

Volumn 8, Issue 26, 2006, Pages 5943-5946

Copper(I)-catalyzed enantio- and diastereoselective tandem reductive aldol reaction

(4) Chuzel, Olivier a Deschamp, Julia a Chausteur, Christophe a Riant, Olivier a

a UNIVERSITÉ CATHOLIQUE DE LOUVAIN (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; COPPER; LIGAND;

ARTICLE; CATALYSIS; CHEMISTRY; STEREOISOMERISM;

ALDEHYDES; CATALYSIS; COPPER; LIGANDS; STEREOISOMERISM;

EID: 33846137282 PISSN: 15237060 EISSN: None Source Type: Journal
DOI: 10.1021/ol062398v Document Type: Article

Times cited : (83)

References (37)

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32
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- After our submission, Shibasaki reported a similar catalytic system for the reductive aldol reaction: (b) Zhao, D. B.; Oisaki, K.; Kanai, M.; Shibasaki, M. Tetrahedron Lett. 2006, 47, 1403.
- After our submission, Shibasaki reported a similar catalytic system for the reductive aldol reaction: (b) Zhao, D. B.; Oisaki, K.; Kanai, M.; Shibasaki, M. Tetrahedron Lett. 2006, 47, 1403.

33
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- The complex was prepared according to a literature procedure, see: Gulliver, D. J.; Levason, W.; Webster, M. Inorg. Chim. Acta 1981, 52, 153. The amount of methanol molecules was determined by single-crystal X-ray crystallographic analysis of the complex (unpublished results).

34
- 33846174735
- 3h Conversion, chemo-, diastereo-, and enantioselectivities were determined by chiral GC. Analytical gas chromatography was performed on a ThermoFinningan Trace GC, using a CHIRALSIL-DEX CB (25 m, 0.25 mm, 25 μm). The ratios are based upon crude integrations which correspond to the corrected integrations by calibration.
- 3h Conversion, chemo-, diastereo-, and enantioselectivities were determined by chiral GC. Analytical gas chromatography was performed on a ThermoFinningan Trace GC, using a CHIRALSIL-DEX CB (25 m, 0.25 mm, 25 μm). The ratios are based upon crude integrations which correspond to the corrected integrations by calibration.

35
- 33846154387
- For example, monodentate Feringa phosphonite, bidentate Reetz phosphites, and tetradentate Trost ligands gave also good activities but low diastero- and enantioselectivities
- For example, monodentate Feringa phosphonite, bidentate Reetz phosphites, and tetradentate Trost ligands gave also good activities but low diastero- and enantioselectivities.

36
- 33846151141
- General procedure for catalytic reductive aldol reaction: A 10 mL flame-dried round-bottomed flask, equipped with a magnetic stirrer, was charged with CuF(PPh3)3·2MeOH (9.0 mg, 0.01 mmol, ligand (0.01 mmol, and toluene (4.8 mL, The catalyst solution was stirred for 30 min at room temperature and phenylsilane (180 μL, 1.40 mmol) was added at the same temperature. After the solution was cooled at -50°C, methyl acrylate (110 μL, 1.20 mmol) and the corresponding aldehyde (1.00 mmol) were simultaneously added to the solution. The mixture was stirred for 1 h at -50°C under argon. Conversion, dr and ee were followed by gas chromatography (aliquots were hydrolyzed by 1 mL of aqueous NH4F solution and filtered through a plug of silica, The reaction mixture was quenched by adding aqueous NH4F solution (5 mL, The aqueous layer was extracted by diethyl ether (3 x 5 mL, Then, the combined organic layers were washed with brine 2
- 4, filtered, and concentrated under reduced pressure. The crude product was purified by flash chromatography to yield the corresponding adduct.

37
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- Oisaki, K.; Zhao, D.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 7164.
- (2006) J. Am. Chem. Soc , vol.128 , pp. 7164
- Oisaki, K.¹ Zhao, D.² Kanai, M.³ Shibasaki, M.⁴

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