Catalytic Enantioselective Synthesis of C1‐ and C2‐Symmetric Spirobiindanones through Counterion‐Directed Enolate C‐Acylation |
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Authors: | Benjamin F Rahemtulla Hugh F Clark Prof?Dr Martin D Smith |
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Institution: | 1. http://msmith.chem.ox.ac.uk;2. Chemistry Research Laboratory, University of Oxford, Oxford, UK;3. GlaxoSmithKline Pharmaceuticals, Medicines Research Centre, Hertfordshire, UK |
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Abstract: | A catalytic enantioselective route to C1‐ and C2‐symmetric 2,2′‐spirobiindanones has been realized through an intramolecular enolate C‐acylation. This reaction employs a chiral ammonium counterion to direct the acylation of an in situ generated ketone enolate with a pentafluorophenyl ester. This reaction constitutes the first example of a direct catalytic enantioselective C‐acylation of a ketone and provides an efficient and highly enantioselective route to axially chiral spirobiindanediones. These products can be diastereoselectively derivatized, offering access to a range of functionalized spirocyclic architectures. |
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Keywords: | axial chirality C-acylation counterion enantioselective synthesis organocatalysis phase-transfer |
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