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Action of (2‐benzothiazolyl) methyllithium with organic polar functions
Author(s) -
Costa Maria Virginia,
Brembilla Alain,
Roizard Denis,
Lochon Pierre
Publication year - 1991
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.5570280612
Subject(s) - methyllithium , chemistry , enamine , electrophile , intramolecular force , alcohol , organic chemistry , amine gas treating , enol , stereoselectivity , medicinal chemistry , catalysis
(2‐Benzothiazolyl) methyllithium reacts quickly at low temperature (‐78°) with a variety of organic electrophiles like aldehydes, ketones, carboxylic esters, nitriles and acylchlorides. Such reactions lead to an easy introduction of alcohol, keto‐enol or amine‐enamine functional groups in extracyclic position with a stereoselective preference. These polyfunctional compounds whose synthesis is difficult by other pathways, are interesting, in particular, because of their ability to form intramolecular hydrogen bonds.