Highly diastereoselective Friedel-Crafts reaction of furans with 8-phenylmenthyl glyoxylate.
The Friedel-Crafts reaction of (1R)-8-phenylmenthyl glyoxylate with variously substituted furans was found to be efficiently promoted by SnCl(4) or magnesium salts with high diastereoselectivities. MgBr(2) performs especially well under simple, undemanding conditions, giving both high yields and high diastereoselectivities (>90%). The reaction afforded chiral substituted furan-2-yl-hydroxyacetic acid esters, compounds of potentially high synthetic interest. [reaction: see text]
Kwiatkowski
Piotr
P
Institute of Organic Chemistry, Polish Academy of Sciences, 01-224 Warsaw, Poland.
Majer
Jakub
J
Chaładaj
Wojciech
W
Jurczak
Janusz
J