NEW TRIALKYLSILYL ENOL ETHER CHEMISTRY - ALPHA-N-TOSYLAMINATION OF TRIISOPROPYLSILYL ENOL ETHERS

Authors
MAGNUS P LACOUR J COLDHAM I MUGRAGE B BAUTA WB
Citation
P. Magnus et al., NEW TRIALKYLSILYL ENOL ETHER CHEMISTRY - ALPHA-N-TOSYLAMINATION OF TRIISOPROPYLSILYL ENOL ETHERS, Tetrahedron, 51(41), 1995, pp. 11087-11110
Citations number
89
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
51
Issue
41
Year of publication
1995
Pages
11087 - 11110
Database
ISI
SICI code
0040-4020(1995)51:41<11087:NTEEC->2.0.ZU;2-V
Abstract
Triisopropylsilyl enol ethers react with (TsN)(2)Se to give alpha-N-to sylamino derivatives in modest to good yields. In the absence of 1,3-d iaxial interactions the N-tosylamino group prefers an axial conformati on. The axial N-tosylamino derivatives can be readily transformed into the azabicyclo[3.3.1]nonane skeleton. the core structure of a number of alkaloids.