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Nucleophile Aminoalkylierung mit Thiopivalamiden
Author(s) -
Lubosch Winfried,
Seebach Dieter
Publication year - 1980
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19800630111
Subject(s) - chemistry , nucleophile , reagent , hydrolysis , medicinal chemistry , primary (astronomy) , table (database) , leaving group , nucleophilic addition , stereochemistry , organic chemistry , catalysis , physics , astronomy , computer science , data mining
Nucleophilic Aminoalkylation with Thiopivalamides Vorläufige Mitt. [1]. Of the twelve thioamides 7a‐e and 8a‐g , only N,N ‐dimethylthiopivalamide ( 7a ) could be metallated at the CH‐group in a ‐position to the N‐Atom. The reagent 9 thus obtained (Table 1) reacts in high yields with primary haloalkanes, with aldehydes, and with non‐enolizable ketones (Table 2) . As shown in Scheme 1 , the products can be hydrolyzed to pivalamides, cleaved to secondary amines, or reduced to neopentylamines (see 18/19, 15 /equation (4) and (5), and 16/20 , respectively).