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Efficient 1,5‐Chirality Transfer in Palladium‐Catalyzed Allylic Alkylations of Chelated Amino Acid Ester Enolates
Author(s) -
Kazmaier Uli,
Lindner Thomas
Publication year - 2005
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/anie.200500095
Subject(s) - stereocenter , allylic rearrangement , palladium , chirality (physics) , diastereomer , chelation , chemistry , stereoselectivity , tsuji–trost reaction , catalysis , olefin fiber , stereochemistry , amino acid , organic chemistry , enantioselective synthesis , physics , biochemistry , chiral symmetry breaking , quantum mechanics , quark , nambu–jona lasinio model
Neither the olefin geometry nor the configuration of secondary allylic substrates in palladium‐catalyzed allylic alkylations of chelated enolates has an influence on the newly formed stereogenic center of the amino acid (see scheme, TBDPS= tert ‐butyldiphenylsilyl, Tfa=trifluoroacetyl). This is controlled exclusively by the protecting group on the chiral center. Therefore, the choice of the protecting group on the allylic alcohol can lead to either of the diastereomeric amino acids in a highly stereoselective fashion.