Kinetic and thermodynamic stereocontrol in the atroposelective formation of sulfoxides by oxidation of 2-sulfanyl-1-naphthamides

Mark S. Betson; Jonathan Clayden; Madeleine Helliwell; David Mitjans

doi:10.1039/B511452G

skip RSC | ChemSpider | Feedback

Home > Journals > Organic & Biomolecular ... > Kinetic and thermodynam...

Authors & Referees | Librarians

You do not have JavaScript enabled. Please enable JavaScript to access the full features of the site or access our non-JavaScript page.

Organic & Biomolecular Chemistry

Issue 21, 2005

More about this Journal
Editorial Board
Submit an Article

Follow Journal | |

Journal Home | RSC Journals

Paper

Previous Article | Next Article

Kinetic and thermodynamic stereocontrol in the atroposelective formation of sulfoxides by oxidation of 2-sulfanyl-1-naphthamides

Mark S. Betson , Jonathan Clayden , Madeleine Helliwell and David Mitjans

Org. Biomol. Chem., 2005, 3, 3898-3904

DOI: 10.1039/B511452G
Received 11 Aug 2005, Accepted 07 Sep 2005
First published on the web 28 Sep 2005

Please wait while Download options loads

Request Permissions

Abstract
Cited by
Related Content

Atropisomeric aromatic amides bearing 2-sulfanyl groups are oxidised by m-CPBA to the corresponding sulfoxides apparently with very high diastereoselectivity. NMR studies and oxidations of chiral benzamides however indicate that the kinetic selectivity of the oxidation is in fact relatively poor, and that the final diastereoisomeric ratio (typically >99∶1) is under thermodynamic control, with relatively unhindered Ar–CO rotation readily converting the less stable to the more stable product diastereoisomer. Molecular mechanics indicates that the thermodynamic diastereoselectivity results principally from electrostatic repulsion between the C [double bond, length as m-dash] O and S–O dipoles.

Supplementary Info

Crystal structure data
TXT (20K)

Terms & Conditions|Privacy |Accessibility|ACAP Enabled

Organic & Biomolecular Chemistry

Kinetic and thermodynamic stereocontrol in the atroposelective formation of sulfoxides by oxidation of 2-sulfanyl-1-naphthamides

Log in (Free Access)

Log in (Subscriber Access)

Supplementary Info

Articles By