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Catalytic Enantioselective Synthesis of C 1 ‐ and C 2 ‐Symmetric Spirobiindanones through Counterion‐Directed Enolate C ‐Acylation
Author(s) -
Rahemtulla Benjamin F.,
Clark Hugh F.,
Smith Martin D.
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201607731
Subject(s) - enantioselective synthesis , acylation , counterion , chemistry , ketone , catalysis , intramolecular force , organocatalysis , combinatorial chemistry , stereochemistry , organic chemistry , ion
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.