Facile preparation of (phosphorylalkyl)-functionalized cyclopropanols and cyclopropylamines

Authors
Winsel, H Gazizova, V Kulinkovich, O Pavlov, V de Meijere, A
Citation
H. Winsel et al., Facile preparation of (phosphorylalkyl)-functionalized cyclopropanols and cyclopropylamines, SYNLETT, (12), 1999, pp. 1999-2003
Citations number
39
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
09365214 → ACNP
Issue
12
Year of publication
1999
Pages
1999 - 2003
Database
ISI
SICI code
0936-5214(199912):12<1999:FPO(CA>2.0.ZU;2-8
Abstract
The reactions of esters 1 and dialkylamides 8 of 3-phosphorylpropionic acid s with Grignard reagents 6 in the presence of titanium tetraisopropoxide 5 or methyltitanium triisopropoxide 11 give 1-substituted and 1,2-disubstitut ed phosphorylated cyclopropanols 7 and cyclopropylamines 12 in moderate to very good yields (37-71 and 39-86%, respectively). These useful transformat ions convincingly demonstrate the wide functional group compatibility and v ersatility of this new carbonyl group cyclopropanation.