Point-to-helical chirality transfer for a scalable and resolution-free synthesis of a helicenoidal DMAP organocatalyst

M.R. Crittall, N.W.G. Fairhurst, D.R. Carbery

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Abstract

The synthesis of a second-generation [6]-helicenoidal DMAP organocatalyst is reported. The synthesis is reliant upon a highly diastereoselective Rh-catalysed [2 + 2 + 2] triyne cycloisomerization, using an existing stereocentre to control the sense of forming helicity. Taken together, a scalable (>1 g), resolution-free entry to a helical DMAP with the capacity for subsequent functionalization, has been achieved.
Original languageEnglish
Pages (from-to)11181-11183
Number of pages3
JournalChemical Communications
Volume48
Issue number91
DOIs
Publication statusPublished - 25 Nov 2012

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