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Asymmetric Synthesis of α‐Methyl α‐Amino Acids by Diastereoselective Alkylation of Optically Active 6‐Isopropyl‐3‐methyl‐2,3—dihydro‐6 H ‐1,4‐oxazin‐2‐ones
Author(s) -
Chinchilla Rafael,
Falvello Larry R.,
Galindo Nuria,
Nájera Carmen
Publication year - 1997
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.199709951
Subject(s) - alkylation , isopropyl , chemistry , catalysis , hydrolysis , optically active , alanine , amino acid , stereochemistry , organic chemistry , medicinal chemistry , biochemistry
At room temperature already highly diastereoselective alkylation of the new, cyclic, chiral alanine ester derivatives (6 R )‐ 1 can been achieved with either K 2 CO 3 as base under solid–liquid phase‐transfer catalysis or Pd catalysis unter neutral conditions. The products (3 S ,6 R )‐ 2 can be easily hydrolyzed to form ( S )‐α‐methyl α‐amino acids.