Catalytic Enantioselective Synthesis of C - and C -Symmetric Spirobiindanones Through Counterion-Directed Enolate C-Acylation

Overview

Journal Angew Chem Int Ed Engl

Specialty Chemistry

Date 2016 Sep 16

PMID 27628946

Citations 3

Authors

Benjamin F Rahemtulla

Hugh F Clark

Martin D Smith

Affiliations

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Abstract

A catalytic enantioselective route to C - and C -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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Catalytic Enantioselective Synthesis of C - and C -Symmetric Spirobiindanones through Counterion-Directed Enolate C-Acylation.

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