DIASTEREOSELECTIVE [3-ACYLIMINOESTERS OBTAINED FROM METHYL 4-METHOXY-2-IMIDAZOLIDINONE AND 2-OXAZOLIDINONE-4-CARBOXYLATES(2] CYCLOADDITION OF ALLYLTRIALKYLSILANES TO INTERMEDIATE N)

Authors
STAHL A STECKHAN E NIEGER M
Citation
A. Stahl et al., DIASTEREOSELECTIVE [3-ACYLIMINOESTERS OBTAINED FROM METHYL 4-METHOXY-2-IMIDAZOLIDINONE AND 2-OXAZOLIDINONE-4-CARBOXYLATES(2] CYCLOADDITION OF ALLYLTRIALKYLSILANES TO INTERMEDIATE N), Tetrahedron letters, 35(40), 1994, pp. 7371-7374
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
40
Year of publication
1994
Pages
7371 - 7374
Database
ISI
SICI code
0040-4039(1994)35:40<7371:D[OFM4>2.0.ZU;2-M
Abstract
The amidoalkylation reaction of methyl 4-methoxy-2-imidazolidinone-4-c arboxylates or methyl 4-methoxy-2-oxazolidinone-4-carboxylates using a llylsilanes as nucleophiles in the presence of TiCl4 affords three car bon ring annulation products 5 and 9 via a [3+2] cycloaddition. Beside s that, the simple methoxy group substitution product is formed. The r ing annulation occurs with practically total diastereoselectivity so t hat all substituents are located on the beta-side of the bicyclic prod uct.