Palladium catalysis in bridge-forming reactions between stereoselectively substituted glycine auxiliaries

The disulfide bridge in cystine has formally been replaced by substitution of two α-alanines at the β-carbon into the 2,3-positions in 1,3-butadiene. The key reactions are stereoselective alkylation of lithiated (2 S)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine with 2,3-dibromopropene. The alkene-...

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Bibliographic Details
Published inTetrahedron Vol. 52; no. 26; pp. 8807 - 8812
Main Authors Møller, Bjørg S., Benneche, Tore, Undheim, Kjell
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 1996
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
DERIVATIVES
ASYMMETRIC-SYNTHESIS
ACID
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Summary:The disulfide bridge in cystine has formally been replaced by substitution of two α-alanines at the β-carbon into the 2,3-positions in 1,3-butadiene. The key reactions are stereoselective alkylation of lithiated (2 S)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine with 2,3-dibromopropene. The alkene-alkene bond formation was effected by Pd-catalysis either with the 2′-bromoallyl products from the alkylation as substrate or with the corresponding amino acid appropriately protected. ( R, R)-2,7-Diamino-4,5-bis(methylene)octanedioic acid and derivatives have been prepared by stereoselective syntheses as analogues of cystine.
ISSN:0040-4020
1464-5416
DOI:10.1016/0040-4020(96)00422-X