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Synthesis of Chiral γ,δ‐Unsaturated Amino Acids by Asymmetric Ester Enolate Claisen Rearrangement
Author(s) -
Kazmaier Uli,
Krebs Achim
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.199520121
Subject(s) - allylic rearrangement , claisen rearrangement , chemistry , carroll rearrangement , asymmetric induction , amino acid , alkyl , recrystallization (geology) , organic chemistry , stereochemistry , medicinal chemistry , enantioselective synthesis , catalysis , biology , biochemistry , paleontology
Ester enolate Claisen rearrangement of the N‐protected amino acid allylic esters 1 affords the corresponding chiral α‐allylic amino acids 2 in excellent yields and selectivities. The quinine used for the induction can be almost completely recovered in the workup. Recrystallization with 1‐phenylethylamine gives enantiomerically pure 2 . R = alkyl, phenyl.
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