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Enantioselective Catalyst Systems from Copper(II) Triflate and BINOL–Silanediol
Author(s) -
Guan Yong,
Attard Jonathan W.,
Visco Michael D.,
Fisher Thomas J.,
Mattson Anita E.
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201801304
Subject(s) - enantioselective synthesis , trifluoromethanesulfonate , catalysis , copper , chemistry , lewis acids and bases , enantiomeric excess , adduct , yield (engineering) , organic chemistry , enantiomer , combinatorial chemistry , materials science , metallurgy
Silanediol and copper catalysis are merged, for the first time, to create an enhanced Lewis acid catalyst system for enantioselective heterocycle functionalization. The promise of this silanediol and copper catalyst combination is demonstrated in the enantioselective addition of indoles to alkylidene malonates to give rise to the desirable adducts in excellent yield and high enantiomeric excess. From these studies, 1,1′‐bi‐2‐naphthol (BINOL)‐based silanediols emerge as one‐of‐a‐kind cocatalysts. Their potential role in the reaction pathway is also discussed.