Highly enantioselective oxazaborolidine-catalyzed reduction of 1,3-dicarbonyl compounds: Role of the additive diethylaniline

Organic Letters

Volumn 11, Issue 7, 2009, Pages 1611-1614

  Chein, R J ^a   Yeung, Y Y ^a   Corey, E J ^a  

^a HARVARD UNIVERSITY   (United States)

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Indexed keywords

EID: 64349102958     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900258f     Document Type: Article

References (5)

1. Yeung, Y.-Y.; Chein, R.-J.; Corey, E. J. J. Am. Chem. Soc. 2007, 129, 10346-10347.
2. Corey, E. J.; Helal, C. J. Angew. Chem., Int. Ed. 1998, 37, 1986-2012.
3. See, Jones, T. K.; Mohan, J. J.; Xavier, L. C.; Blacklock, T. J.; Mathre, D. J.; Sohar, P.; Jones, E. T. T.; Reamer, R. A.; Roberts, F. E.; Grabowski, E. J. J. J. Org. Chem. 1991, 56, 763-769.
4. 2 (1 M in toluene, 1.0 mL, 1.0 mmol) at 23 °C. The resulting solution was heated to 40 °C for 1 h. After stirring at 23 °C for another 1 h, solvents were removed in vacuo (ca. 0.1 mmHg). The residue was diluted with benzene (2 mL) and the suspension was filtered through a sintered glass funnel under nitrogen. The ammonium salt was washed with benzene (5mL) and the benzene was removed in vacuo (ca. 0.1 mmHg). Toluene (5.0 mL) was added to provide a 0.20 M solution of the pure oxazaborolidine 3.
5. Soundararajan, R.; Matteson, D. S. J. Org. Chem. 1990, 55, 2274-2275.