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Zaitsev AB, Adolfsson H. Enantioswitchable catalysts for the asymmetric transfer hydrogenation of aryl alkyl ketones. Org Lett. 2006;8(22):5129-32doi: 10.1021/ol062227q.
Zaitsev, A. B., & Adolfsson, H. (2006). Enantioswitchable catalysts for the asymmetric transfer hydrogenation of aryl alkyl ketones. Organic letters, 8(22), 5129-32. https://doi.org/10.1021/ol062227q
Zaitsev, Alexey B, and Adolfsson, Hans. "Enantioswitchable catalysts for the asymmetric transfer hydrogenation of aryl alkyl ketones." Organic letters vol. 8,22 (2006): 5129-32. doi: https://doi.org/10.1021/ol062227q
Zaitsev AB, Adolfsson H. Enantioswitchable catalysts for the asymmetric transfer hydrogenation of aryl alkyl ketones. Org Lett. 2006 Oct 26;8(22):5129-32. doi: 10.1021/ol062227q. PMID: 17048860.
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Org Lett. 2006 Oct 26;8(22):5129-32. doi: 10.1021/ol062227q.

Enantioswitchable catalysts for the asymmetric transfer hydrogenation of aryl alkyl ketones.

Organic letters

Alexey B Zaitsev, Hans Adolfsson

Affiliations

  1. Department of Organic Chemistry, Stockholm University, The Arrhenius Laboratory, SE-10691 Stockholm, Sweden.

PMID: 17048860 DOI: 10.1021/ol062227q

Abstract

A subtle change in the ligand structure, replacing the carbonyl oxygen with sulfur in simple alpha-amino acid amides, resulted in a dramatic activity and selectivity improvement in the rhodium- or ruthenium-catalyzed reduction of ketones under hydrogen transfer conditions. In addition, in most cases, a switch of the product's absolute configuration was observed on going from amides to the corresponding thioamides. Under optimized conditions, we obtained the secondary alcohol products in high yield and enantioselectivity (up to 97% ee) using only 0.25 mol % catalyst loading. [structure: see text]

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