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C 2 ‐Symmetric Cationic Copper( II ) Complexes as Chiral Lewis Acids: Counterion Effects in the Enantioselective Diels–Alder Reaction
Author(s) -
Evans David A.,
Murry Jerry A.,
von Matt Peter,
Norcross Roger D.,
Miller Scott J.
Publication year - 1995
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199507981
Subject(s) - counterion , cationic polymerization , enantioselective synthesis , chemistry , lewis acids and bases , copper , catalysis , medicinal chemistry , diels–alder reaction , polymer chemistry , organic chemistry , stereochemistry , ion
Alone a tailor‐made chiral cationic Lewis acid is not sufficient to achieve high enantiomic excesses in Diels–Alder reactions; the counterion can dramatically affect the efficiency of the chiral catalyst. Thus, for example, the enantioselectivities reached in these reactions in the presence of the copper complex 1 with X = SbF 6 as counterion are in some cases substantially greater than those with X = OSO 2 CF 3 .