Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2007 Aug 13;48(33):5799-5802.
doi: 10.1016/j.tetlet.2007.06.086.

Enantioselective Reduction of Prochiral Ketones using Spiroborate Esters as Catalysts

Viatcheslav Stepanenko  1 , Melvin De Jesus, Wildeliz Correa, Irisbel Guzman, Cindybeth Vazquez, Wilanet de la Cruz, Margarita Ortiz-Marciales, Charles L Barnes
Affiliations

Enantioselective Reduction of Prochiral Ketones using Spiroborate Esters as Catalysts

Viatcheslav Stepanenko et al. Tetrahedron Lett. .

Abstract

Novel spiroborate esters derived nonracemic 1,2-aminoalcohols and ethylene glycol are reported as highly effective catalysts for the asymmetric borane reduction of a variety of prochiral ketones with borane-dimethyl sulfide complex at room temperature. Optically active alcohols were obtained in excellent chemical yields using 0.1 to 10 mol % of catalysts with up to 99% ee.

PubMed Disclaimer

Figures

Fig. 1
Fig. 1
Crystal structure of spiroborate 1.
Fig. 2
Fig. 2
Asymmetric reduction of acetophenone in the presence of catalyst 1.
Scheme 1
Scheme 1
See this image and copyright information in PMC

References

    1. Silverman RB. The Organic Chemistry of Drug Design and Drug Action. Elsevier Academic Press; Burlington, MA: 2004.
    2. Challenger CA. Chiral Drugs. John Wiley & Sons; New york: 2001.
    1. Ager DJ. Chiral Chemicals. Marcel Dekker, Inc; New York: 1999.
    1. Morris DJ, Hayes AM, Wills M. J Org Chem. 2006;71:7035–7044. - PubMed
    1. Schiffers I, Rantanen T, Schmidt F, Bergmans W, Zani L, Bolm C. J Org Chem. 2006;71:2320–2331. - PubMed
    1. Boren L, Martin-Matute B, Xu Y, Cordova A, Backvall JE. Chem Eur J. 2006;12:225–232. - PubMed
    2. Zhu D, Hua L. J Org Chem. 2006;71:9484–9486. - PubMed
    3. Zhu D, Yang Y, Buynak JD, Hua L. Org & Biomol Chem. 2006;4:2690–2695. - PubMed

LinkOut - more resources