A 3-STEP, HIGHLY ENANTIOSELECTIVE SYNTHESIS OF (R)-2-METHYL TRYPTOPHANE ETHYL-ESTER - COMPARISON WITH CHEMICAL RESOLUTION

Authors
SOLLADIECAVALLO A SCHWARZ J MOUZA C
Citation
A. Solladiecavallo et al., A 3-STEP, HIGHLY ENANTIOSELECTIVE SYNTHESIS OF (R)-2-METHYL TRYPTOPHANE ETHYL-ESTER - COMPARISON WITH CHEMICAL RESOLUTION, Tetrahedron letters, 39(22), 1998, pp. 3861-3864
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
22
Year of publication
1998
Pages
3861 - 3864
Database
ISI
SICI code
0040-4039(1998)39:22<3861:A3HESO>2.0.ZU;2-O
Abstract
(R)-2-Methyltryptopban ethyl ester, (R)-2, having an enantiomeric puri ty >,=96% was obtained in 3 steps and using (SSS)-hydroxypinanone, 1, as the recoverable chiral auxiliary. The synthesis of the alkylating a gent, 5a, was improved (to a reproduceble 55% overall yield from 2,3-d imethylindole). The resolution of racemic-2 through chromatographic se paration of the corresponding iminoester derived from (RRR)-1 also pro ved to be easy and efficient (similar to 25% yield). (C) 1998 Elsevier Science Ltd. All rights reserved.