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Highly Efficient Asymmetric Additions of Diethylzinc to Aldehydes Triply Activated by Chiral Phosphoramide‐Zn(II) Complexes Derived From Cinchona Alkaloids
Author(s) -
Shen Bin,
Huang Huayin,
Bian Guangling,
Zong Hua,
Song Ling
Publication year - 2013
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22171
Subject(s) - diethylzinc , chemistry , enantioselective synthesis , lewis acids and bases , chirality (physics) , enantiomer , catalysis , organic chemistry , chiral lewis acid , cinchona alkaloids , alcohol , cinchona , combinatorial chemistry , medicinal chemistry , chiral symmetry breaking , physics , quantum mechanics , quark , nambu–jona lasinio model
New chiral phosphoramide ligands derived from cinchona alkaloids were developed, which react with diethylzinc to form chiral phosphoramide‐Zn(II) complexes containing two Lewis bases and one Lewis acid. These trifunctional complexes can serve as highly efficient chiral catalysts for triple activation of enantioselective addition reactions of diethylzinc with aldehydes to give desired alcohol products with excellent yields and enantiomeric excess ( ee ) values up to 99%. Chirality 25:561‐566, 2013 . © 2013 Wiley Periodicals, Inc.