1.
Org Lett
; 2(14): 2015-7, 2000 Jul 13.
Artigo
em Inglês
| MEDLINE
| ID: mdl-10891218
RESUMO
A new aspect of commonly used BF(3).OEt(2) has been illuminated by successfully demonstrating the unique but highly stereoselective reactions of hydroxy carbonyl and dicarbonyl substrates. For example, treatment of gamma-hydroxy ketone 1c with BF(3).OEt(2)/Bu(3)SnH in CH(2)Cl(2) at -78 to -40 degrees C afforded the corresponding 1, 4-diol 2c with virtually complete diastereoselection, while use of TiCl(4) as a Lewis acid under similar reaction conditions caused a total lack of diol yield and selectivity (17%; 2c/3c = 1.2:1), accompanied by a significant formation of 2,3-disubstituted tetrahydrofuran 4 (44%).