AMINOSILANES IN ORGANIC-SYNTHESIS - ADDITION OF ORGANOCOPPER REAGENTSON GAMMA-BIS(TRIMETHYLSILYL)AMINO-ALPHA-ACETYLENIC AMIDES, ESTERS ANDKETONES - STEREOCHEMISTRY AND SOME SYNTHETIC USES

Authors
CORRIU RJP BOLIN G IQBAL J MOREAU JJE VERNHET C
Citation
Rjp. Corriu et al., AMINOSILANES IN ORGANIC-SYNTHESIS - ADDITION OF ORGANOCOPPER REAGENTSON GAMMA-BIS(TRIMETHYLSILYL)AMINO-ALPHA-ACETYLENIC AMIDES, ESTERS ANDKETONES - STEREOCHEMISTRY AND SOME SYNTHETIC USES, Tetrahedron, 49(21), 1993, pp. 4603-4618
Citations number
73
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
49
Issue
21
Year of publication
1993
Pages
4603 - 4618
Database
ISI
SICI code
0040-4020(1993)49:21<4603:AIO-AO>2.0.ZU;2-3
Abstract
The stereochemical outcome of the carbocupration of gamma-bis(trimethy lsilyl)amino-alpha-acetylenic amide, esters and ketone was studied. A judicious choice of substrate, reagent and(or) reaction conditions all ows to perform highly stereoselective cis or trans addition. The inter mediate vinylic copper adducts, with (E) or (Z) configuration, react w ith electrophilic reagents to provide short routes to substituted pyrr olinones and pyrroles.