Allene Relay: Palladium‐Catalyzed Bicyclization of Allene‐Propargylic Carbonates with Geminal Bis(nucleophile)s1. Issue 41 (22nd August 2013)

• Record Type: Journal Article
• Authors: Ye, Juntao; Ma, Shengming
• Is Part Of: Angewandte Chemie international edition. Volume 52:Issue 41(2013)
• Page Start: 10809
• Page End: 10813
• Publication Date: 2013-08-22
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201304950
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="graphical" xml:lang="en"> <title> <x xml:space="preserve">Abstract</x> </title> <p> <bold>Pass the baton</bold>: The title reaction affords synthetically attractive bicyclo[4.3.0] skeletons in up to 85 % yield by three consecutive CC bond formations in a single operation (see scheme; DMF=<italic>N</italic>, <italic>N</italic>‐dimethylformamide, DMSO=dimethyl sulfoxide, Ts=4‐toluenesulfonyl). The challenge of efficient axial‐to‐central chirality transfer involving π‐allyl palladium intermediates has been also realized. Mechanistic studies are discussed.<boxed-text content-type="graphic" position="anchor" orientation="portrait"><graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgg3j1p0mgh" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /></boxed-text></p> </abstract>