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Highly Enantioselective Desymmetrization of Anhydrides by Carbon Nucleophiles: Reactions of Grignard Reagents in the Presence of (−)‐Sparteine
Author(s) -
Shintani Ryo,
Fu Gregory C.
Publication year - 2002
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 - 10.1002/1521-3773(20020315)41:6<1057::aid-anie1057>3.0.co;2-h
Subject(s) - sparteine , enantioselective synthesis , reagent , chemistry , desymmetrization , nucleophile , electrophile , grignard reagent , combinatorial chemistry , organic chemistry , catalysis
Where other common chiral ligands failed , (−)‐sparteine can be employed to form complexes with Grignard reagents. These chirally modified reagents desymmetrize a range of anhydrides with good enantioselectivity (up to 92 % ee ; see scheme). Whereas (−)‐sparteine is well known to form complexes with organolithium reagents and to induce excellent enantioselection in their reactions with electrophiles, (−)‐sparteine‐controlled asymmetric processes that involve Grignard reagents are rare.