Synthesis of tryptophans by alkylation of chiral glycine enolate equivalents with quaternary gramines

[Display omitted] Quaternary gramines were found to be a suitable source of the 3-methylindole fragment for diastereoselective alkylation. The best yields and stereoselectivity were obtained for the alkylation of a chiral William’s morpholinone enolate. Based on this transformation, a general method...

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Bibliographic Details
Published inTetrahedron letters Vol. 56; no. 43; pp. 5882 - 5885
Main Authors Reinfelds, Matiss, Kalinins, Konstantins, Katkevica, Dace, Zemribo, Ronalds, Katkevics, Martins
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 21.10.2015
Elsevier
Subjects
Chemistry
Chemistry, Organic
Diastereoselective alkylation
Gramine
Physical Sciences
Science & Technology
Tryptophan
Williams’ morpholinone
Tryptophan
Williams’ morpholinone
Gramine
Diastereoselective alkylation
Williams' morpholinone
ASYMMETRIC-SYNTHESIS
ENANTIOSELECTIVE SYNTHESIS
ANALOGS
ALPHA-AMINO-ACIDS
DERIVATIVES
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Summary:[Display omitted] Quaternary gramines were found to be a suitable source of the 3-methylindole fragment for diastereoselective alkylation. The best yields and stereoselectivity were obtained for the alkylation of a chiral William’s morpholinone enolate. Based on this transformation, a general method for the synthesis of enantiopure, indole ring substituted tryptophan derivatives was developed with good overall yields.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2015.09.017