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The discovery of new methods for the synthesis of classes of potentially bioactive molecules remains an important goal for synthetic chemists. Vinylsulfonium salts have been used for the synthesis of a wide variety of small heterocyclic motifs; however, further developments to this important class of reagents has been focused on reaction with new substrates rather than development of new vinylsulfonium salts. We herein report the synthesis of a range of α-substituted vinylsulfonium tetraphenylborates (10 examples) in a 3 step procedure from commercially available styrenes. The important role of the tetraphenylborate counterion on the stability and accessibility of the vinylsulfonium salts is also detailed. The α-substituted vinylsulfonium tetraphenylborates gave good to excellent yields in the epoxyannulation of β-amino ketones (15 examples) and the cyclopropanation of allylic amines (4 examples). Hydrogenation of an epoxyannulation product proceeded with good diastereoselectivity.
|Number of pages||14|
|Journal||Journal of Organic Chemistry|
|Publication status||Published - 7 Nov 2014|
- BCS and TECS CDTs
FingerprintDive into the research topics of 'Synthesis of α-substituted vinylsulfonium salts and their application as annulation reagents in the formation of epoxide- and cyclopropane-fused heterocycles'. Together they form a unique fingerprint.
- 2 Finished
3-month Core Capability for Chemistry Research
1/01/13 → 1/04/13
Changing the Synthesis Landscape with Boron at the Helm: from Chiral Organometallics to Assembly Line Synthesis
14/05/12 → 13/01/18