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First Dynamic Kinetic Resolution of Racemic α‐Amino Aldehydes
Author(s) -
Rein Tobias,
Kreuder Reinhard,
von Zezschwitz Paultheo,
Wulff Christian,
Reiser Oliver
Publication year - 1995
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.199510231
Subject(s) - kinetic resolution , phosphonate , kinetic energy , epimer , yield (engineering) , chemistry , substrate (aquarium) , stereochemistry , organic chemistry , enantioselective synthesis , catalysis , thermodynamics , biology , physics , quantum mechanics , ecology
The configurational instability of α‐amino aldehydes is an advantage for dynamic kinetic resolution (that is, kinetic resolutions with in situ epimerization of the substrate) through the Horner–Wadsworth–Emmons reaction. For instance, rac ‐ 1 and the chiral phosphonate 2 yield the ester ( S )‐ 3 with 90% de . Bn = PhCH 2 , Ts = H 3 CC 6 H 4 SO 2 , R = CF 3 CH 2 , R′ = (−)‐8‐phenylmenthyl.