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Synthesis of Highly Enantio‐Enriched α‐Amino Acids by Carboxylation of N ‐(α‐Lithioalkyl)oxazolidinones
Author(s) -
Jeanjean Fabien,
Fournet Guy,
Bars Didier Le,
Goré Jacques
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200004)2000:7<1297::aid-ejoc1297>3.0.co;2-l
Subject(s) - chemistry , diastereomer , carboxylation , moiety , amino acid , stereochemistry , methionine , alanine , lithium amide , enantioselective synthesis , organic chemistry , catalysis , biochemistry
N ‐(α‐Stannylalkyl)oxazolidinones can be obtained as a mixture of diastereomers in three steps from aldehydes with yields dependent on the R group of R‐CHO. They can be transformed by a tin‐lithium exchange to N ‐(α‐lithioalkyl)oxazolidinones which equilibrate rapidly to one diastereomer. These compounds give rise, after carboxylation, to the diastereopure N ‐(α‐carboxyalkyl)oxazolidinones. Transformation of the oxazolidinone moiety to a free amino group is accomplished by a Birch‐type reduction. Using this method, L ‐methionine, L ‐alanine, L ‐leucine and L ‐homocysteine were obtained in good yields and ee = 92% to ≥ 95%. The short time required for the whole sequence makes this method ideal for synthesising 1‐[ 11 C]amino acids.