Concentration dependence of the sharpless asymmetric amidohydroxylation of isopropyl cinnamate

Organic Letters

Volumn 2, Issue 17, 2000, Pages 2667-2669

  Wuts, Peter G M ^a   Anderson, Andrew M ^a   Goble, Michael P ^a   Mancini, Sarah E ^a   Vanderroest, Ronald J ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001648049     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006198+     Document Type: Article

References (11)

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3. For a review on the semisynthesis of paclitaxel, see: Wuts, P. G. M. Current Opin. Drug Discovery Dev. 1998, 1, 329.
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5. Rubenstein, H.; Svendsen, J. S. Acta Chemica Scand. 1994, 48, 439.
6. Patrick, D. W.; Truesdale, L. K.; Biller, S. A.; Sharpless, K. B. J. Org. Chem. 1978, 43, 2628.
7. Lesser amounts of acetamide gave inconsistent results.
8. Kolb, H. C.; Van Nieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2488.
9. Oliveto, E. P.; Gerold, C. Organic Syntheses: Wiley: New York, 1963: Collect. Vol. IV, p 104.
10. Milas, N. A.; Trepagnier, J. H.; Nolan, J. T., Jr.; Iliopulos M. I. J. Am. Chem. Soc. 1959, 81, 4730.
11. 2. The combined organic layers are stirred with magnesol (20 g) for 30 min and filtered. The organic is distilled to dryness. Methyl terf-butyl ether (20 mL) is added, and the mixture is stirred until a slurry forms. Hexane (20 mL) is added to complete precipitation. The slurry is filtered, washed with 50/50 MTBE/hexane, and dried with nitrogen. (60% yield (8.3 g) >97% ee).