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Alkylation of Amino Acids without Loss of Optical Activity: α‐ and β‐Alkylation of an Aspartic Acid Derivative
Author(s) -
Seebach Dieter,
Wasmuth Daniel
Publication year - 1981
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.198109711
Subject(s) - alkylation , chemistry , aspartic acid , derivative (finance) , diastereomer , enantiomer , amino acid , medicinal chemistry , stereochemistry , organic chemistry , biochemistry , catalysis , financial economics , economics
The α‐alkylation of β‐heterosubstituted carbonyl compounds leads to a surprising result in the case of L ‐(+)‐ N ‐formylaspartic acid di‐ tert ‐butyl ester: A mixture of the β‐ and α‐substituted aspartic acid derivatives ( 1 ) and ( 2 ) ( ca. 7:2) is obtained. The erythro ‐isomers of ( 1 ) are formed stereospecifically, while, interestingly, an enantiomer of ( 2 ) is formed in excess; RCH 3 , C 2 H 5 , CH 2 CHCH 2 , CH 2 C 6 H 5 .