ASYMMETRIC-SYNTHESIS OF UNUSUAL AMINO-ACIDS - SYNTHESIS OF THE OPTICALLY PURE ISOMERS OF INDOLE-PROTECTED BETA-METHYLTRYPTOPHAN SUITABLE FOR PEPTIDE-SYNTHESIS

The four isomers of N-indole-(2-mesitylenesulfonyl)-beta-methyltryptophan have been synthesized in high optical purity using in part, asymmetric conjugate 1, 4-additions followed by chiral imide enolate azidation and reduction.

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Bibliographic Details
Published inTetrahedron letters Vol. 33; no. 49; pp. 7491 - 7494
Main Authors BOTEJU, LW, WEGNER, K, HRUBY, VJ
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 1992
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
10-SULFONAMIDO-ISOBORNYL ESTERS
DESIGN
(E)-ENOYLSULTAMS ENOLATE PROTONATIONS
1,4-ADDITIONS
GILMAN REAGENTS
CONJUGATE ADDITION
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Summary:The four isomers of N-indole-(2-mesitylenesulfonyl)-beta-methyltryptophan have been synthesized in high optical purity using in part, asymmetric conjugate 1, 4-additions followed by chiral imide enolate azidation and reduction.
ISSN:0040-4039
DOI:10.1016/S0040-4039(00)60804-3