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
. 2016 Jan 26;55(5):1816-9.
doi: 10.1002/anie.201507806. Epub 2016 Jan 6.

Stereoelectronic Model To Explain Highly Stereoselective Reactions of Seven-Membered-Ring Oxocarbenium-Ion Intermediates

Matthew G Beaver  1 , Trixia M Buscagan  2 , Olga Lavinda  3 , K A Woerpel  4
Affiliations

Stereoelectronic Model To Explain Highly Stereoselective Reactions of Seven-Membered-Ring Oxocarbenium-Ion Intermediates

Matthew G Beaver et al. Angew Chem Int Ed Engl. .

Abstract

Nucleophilic attack on seven-membered-ring oxocarbenium ions is generally highly stereoselective. The preferred mode of nucleophilic attack forms the product in a conformation that minimizes transannular interactions, thus leading to different stereoselectivity as compared to that of reactions involving six-membered-ring oxocarbenium ions.

Keywords: carbocations; carbohydrates; conformational analysis; electrostatic effects; stereoselectivity.

PubMed Disclaimer

Figures

Chart 1
Chart 1
Chart 2
Chart 2
See this image and copyright information in PMC

Similar articles

See all similar articles

Cited by

See all "Cited by" articles

References

    1. Kleinke AS, Webb D, Jamison TF. Tetrahedron. 2012;68:6999–7018.
    1. Saha J, Peczuh MW. In: Advances in Carbohydrate Chemistry and Biochemistry. Derek H, editor. Vol. 66. Academic; 2011. pp. 121–186. - PubMed

    1. See, for example: Nicolaou KC, Hwang CK, Duggan ME, Nugiel DA, Abe Y, Reddy KB, DeFrees SA, Reddy DR, Awartani RA, Conley SR, Rutjes FPJT, Theodorakis EA. J Am Chem Soc. 1995;117:10227–10238.Castro S, Fyvie WS, Hatcher SA, Peczuh MW. Org Lett. 2005;7:4709–4712.Boone MA, McDonald FE, Lichter J, Lutz S, Cao R, Hardcastle KI. Org Lett. 2009;11:851–854.Fuwa H, Ishigai K, Hashizume K, Sasaki M. J Am Chem Soc. 2012;134:11984–11987.

    1. Entrena A, Campos JM, Gallo MA, Espinosa A. ARKIVOC. 2005;vi:88–108.
    1. Espinosa A, Gallo MA, Entrena A, Gómez JA. J Mol Struct. 1994;323:247–256.

Publication types

LinkOut - more resources