Regioselective synthesis of propargylic primary 1,4-diamines via organozincs and applications

Authors
Courtois, G Desre, V Miginiac, L
Citation
G. Courtois et al., Regioselective synthesis of propargylic primary 1,4-diamines via organozincs and applications, J ORGMET CH, 580(1), 1999, pp. 178-187
Citations number
23
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANOMETALLIC CHEMISTRY
ISSN journal
0022328X → ACNP
Volume
580
Issue
1
Year of publication
1999
Pages
178 - 187
Database
ISI
SICI code
0022-328X(19990515)580:1<178:RSOPP1>2.0.ZU;2-S
Abstract
Reactive organozincs obtained from allylic and propargylic bromides regiose lectively react with the N-trimethylsilylaldimines prepared in situ from th e corresponding carbamates of various alpha-acetylenic gamma-aminoaldehydes to form a new amine function. Thus, we have achieved alpha-acetylenic prim ary 1,4-diamines: H2N-CH(R')-C equivalent to C-CH(R)-NH2 (R not equal R' or R=R'), then alpha-ethylenic primary 1,4-diamines (E) or (Z) through a part ial hydrogenation.