Me3SiBr-mediated intramolecular cyclization of gamma-functionalized trimethylsilyl nitronates.

Authors
Tishkov, AA Kozintsev, AV Lyapkalo, IM Ioffe, SL Kachala, VV Strelenko, YA Tartakovsky, VA
Citation
Aa. Tishkov et al., Me3SiBr-mediated intramolecular cyclization of gamma-functionalized trimethylsilyl nitronates., TETRAHEDR L, 40(27), 1999, pp. 5075-5078
Citations number
19
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
27
Year of publication
1999
Pages
5075 - 5078
Database
ISI
SICI code
0040-4039(19990702)40:27<5075:MICOGT>2.0.ZU;2-6
Abstract
The silylation of nitro compounds of general formula (XXCHCH)-X-1-C-2(Ar)CH 2NO2 with Me3SiBr/Et3N at -30 degrees C leads to hitherto unknown 2-(N,N-bi s(trimethylsilyloxy)amino-2,3-dihydrofurans (X-1=PhCO, X-2=H) or to N,N-bi( trimethylsilyloxy)aminocyclopropanes (X-1=X-2=COOMe). N,N-Bis(trimethylsily loxy)immonium cations appear to be the key intermediates in this process. ( C) 1999 Elsevier Science Ltd. All rights reserved.