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Kinetic Resolution of the Acrolein Dimer by Asymmetric Horner‐Wadsworth‐Emmons Reactions
Author(s) -
Rein Tobias,
Kann Nina,
Kreuder Reinhard,
Gangloff Benoit,
Reiser Oliver
Publication year - 1994
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.199405561
Subject(s) - acrolein , dimer , chemistry , kinetic resolution , kinetic energy , medicinal chemistry , stereochemistry , organic chemistry , catalysis , enantioselective synthesis , physics , quantum mechanics
Diastereoselectivities up to 98% de have been reached in kinetic resolutions of the racemic acrolein dimer 1 by reaction with the chiral phosphonates 2 . Depending on the choice of substituents on the phosphoryl group (R CF 3 CH 2 , C 2 H 5 ), either ( E )‐ 3 or ( Z )‐ 3 , both of which are versatile synthetic building blocks, can be obtained as the major product. The dominant isomer for ( Z )‐ 3 is the ( S ) isomer and for ( E )‐ 3 the ( R ) isomer.
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