Asymmetric synthesis with a chiral catalyst generated from asymmetric autocatalysis

Organic Letters

Volumn 3, Issue 24, 2001, Pages 3851-3853

  Sato, Itaru ^a   Urabe, Hiroki ^a   Ishii, Shinji ^a   Tanji, Shigehisa ^a   Soai, Kenso ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

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ARTICLE;

EID: 0000923656     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0166350     Document Type: Article

References (49)

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47. 2Zn (0.5 mmol) were added successively, and the mixture was stirred for an additional 15 min. After the solution was cooled to 0°C. a toluene (2.6 mL) solution of pyridine-3-carbaldehyde 3a (53.5 mg, 0.5 mmol) was added to the solution over a period of 2 h using a microfeeder, and the mixture was stirred at 0°C for 19 h. The reaction was quenched by the addition of saturated aqueous sodium chloride (15 mL). The mixture was filtered using Celite, and the filtrate was extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure. Purification of the residue by silica gel thin-layer chromatography (developing solvent, hexane:ethyl acetate = 1:1 v/v) gave (S)-2-methyl-1-(3-pyridyl)-propan-1-ol 4a with 96% ee in an isolated yield of 84% (63.1 mg). In addition, the recovered (S)-5-pyrimidyl alkanol 2a was found to have 92% ee.
48. 2Zn (0.6 mmol) at 0°C. A toluene (2.6 mL) solution of 3a (94.1 mg, 0.5 mmol) was then added over a period of 2 h using a microfeeder, and the mixture was stirred for 18 h at 0°C. The reaction was quenched by the addition of saturated aqueous sodium chloride (15 mL). The mixture was filtered using Celite, and the filtrate was extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure. Purification of the residue by silica gel thin-layer chromatography (developing solvent, hexane:ethyl acetate = 1:1 v/v) gave (S)-4a with 9% ee in an isolated yield of 70% (53.1 mg).
49. Soai, K.; Tanji, S.; Kodaka Y.; Shibata, T. Enantiomer 1998, 3, 241-243.