CaltechAUTHORS
Published January 6, 2014 | Version Supplemental Material
Journal Article Open

Catalyst-Controlled Wacker-Type Oxidation: Facile Access to Functionalized Aldehydes

Creators

  • 1. ROR icon California Institute of Technology

Abstract

The aldehyde-selective oxidation of alkenes bearing diverse oxygen groups in the allylic and homoallylic position was accomplished with a nitrite-modified Wacker oxidation. Readily available oxygenated alkenes were oxidized in up to 88% aldehyde yield and as high as 97% aldehyde selectivity. The aldehyde-selective oxidation enabled the rapid, enantioselective synthesis of an important pharmaceutical agent, atomoxetine. Finally, the influence of proximal functional groups on this anti-Markovnikov reaction was explored, providing important preliminary mechanistic insight.

Additional Information

© 2014 American Chemical Society. Published In Issue January 22, 2014; Article ASAP January 13, 2014; Just Accepted Manuscript January 06, 2014; Received: November 18, 2013. We acknowledge financial support from the Gordon and Betty Moore Foundation, the NSF, and the Swiss National Science Foundation for a fellowship to B.M.

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Supplemental Material - ja411749k_si_001.pdf

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Additional details

Identifiers

Eprint ID
43469
DOI
10.1021/ja411749k
Resolver ID
CaltechAUTHORS:20140122-102842387

Funding

Gordon and Betty Moore Foundation
NSF
Swiss National Science Foundation (SNSF)

Dates

Created
2014-01-29
Created from EPrint's datestamp field
Updated
2021-11-10
Created from EPrint's last_modified field