Catalytic Enantioselective Synthesis of C 1 ‐ and C 2 ‐Symmetric Spirobiindanones through Counterion‐Directed Enolate C ‐Acylation

Abstract A catalytic enantioselective route to C 1 ‐ and C 2 ‐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 es...

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Bibliographic Details
Published inAngewandte Chemie Vol. 128; no. 42; pp. 13374 - 13377
Main Authors Rahemtulla, Benjamin F., Clark, Hugh F., Smith, Martin D.
Format Journal Article
LanguageEnglish
Published 10.10.2016
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Summary:Abstract A catalytic enantioselective route to C 1 ‐ and C 2 ‐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.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201607731