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Optically active heteroaromatic compounds IX . Preparation, absolute configuration and optical purity of some chiral 3‐alkylindoles
Author(s) -
Menicagli Rita,
Malanga Corrado,
Lardicci Luciano
Publication year - 1979
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570160410
Subject(s) - chemistry , stereospecificity , isatin , alkylation , absolute configuration , optically active , grignard reaction , organic chemistry , stereochemistry , combinatorial chemistry , catalysis , reagent
The Fischer and Brunner reactions as well as the Grignard alkylation of isatin have been used to prepare ( S )‐3‐ sec ‐butyl‐ and ( S )‐3‐(2‐methylbutyl)indoles, respectively, starting from ( S )‐1‐chloro‐2‐methylbutane. The stereospecificity of the synthetic sequences followed has been investigated and the stereochemical relationships of the title compounds have been established.