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Wuts PG, Anderson AM, Goble MP, et al. Concentration dependence of the sharpless asymmetric amidohydroxylation of isopropyl cinnamate. Org Lett. 2000;2(17):2667-9doi: 10.1021/ol006198+.
Wuts, P. G., Anderson, A. M., Goble, M. P., Mancini, S. E., & VanderRoest, R. J. (2000). Concentration dependence of the sharpless asymmetric amidohydroxylation of isopropyl cinnamate. Organic letters, 2(17), 2667-9. https://doi.org/10.1021/ol006198+
Wuts, et al. "Concentration dependence of the sharpless asymmetric amidohydroxylation of isopropyl cinnamate." Organic letters vol. 2,17 (2000): 2667-9. doi: https://doi.org/10.1021/ol006198+
Wuts PG, Anderson AM, Goble MP, Mancini SE, VanderRoest RJ. Concentration dependence of the sharpless asymmetric amidohydroxylation of isopropyl cinnamate. Org Lett. 2000 Aug 24;2(17):2667-9. doi: 10.1021/ol006198+. PMID: 10990423.
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Org Lett. 2000 Aug 24;2(17):2667-9. doi: 10.1021/ol006198+.

Concentration dependence of the sharpless asymmetric amidohydroxylation of isopropyl cinnamate.

Organic letters

Wuts, Anderson, Goble, Mancini, VanderRoest

Affiliations

  1. Chemical Process Research and Development, Pharmacia, Kalamazoo, Michigan 49001, USA. [email protected]

PMID: 10990423 DOI: 10.1021/ol006198+

Abstract

[reaction: see text]A need to prepare large quantities of phenylisoserine for the semisynthesis of paclitaxel prompted us to examine the Sharpless amidohydroxylation reaction to see if it could be run at concentrations greater than those reported in the literature. During these investigations, we discovered that the amount of amidoalcohol produced in the reaction decreased while the diol side product increased as the concentration increased. We discovered that acetamide suppresses this side reaction and allows us to run the chemistry at 0.1 g/mL rather than the 0.014 g/mL reported in the literature.

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