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Diastereoselective Mannich Reaction of Chiral Enolates Formed by Enantioselective Conjugate Addition of Grignard Reagents
Author(s) -
Galeštoková Zuzana,
Šebesta Radovan
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201101270
Subject(s) - chemistry , enantioselective synthesis , diastereomer , silylation , imine , mannich reaction , conjugate , enantiomer , enol , reagent , organic chemistry , chiral auxiliary , addition reaction , grignard reaction , catalysis , mathematical analysis , mathematics
Cu–Taniaphos‐catalyzed enantioselective addition of Grignard reagents to cyclic enones leads to chiral magnesium enolates. These enolates add to N ‐protected imines directly, or through in situ transformation to silyl enol ethers. Diastereoselectivity of the addition depends on the nitrogen protecting group of the imine. Diastereoisomers of the resulting β‐amino carbonyl compounds can be separated and are obtained in acceptable yields and in high enantiomeric purities (up to 99:1 er ).