T. Murakami, K. Furusawa
Nov 4, 2002
Citations
0
Influential Citations
41
Citations
Journal
Tetrahedron
Abstract
Abstract A convenient diastereoselective synthesis of d - erythro - and l - threo -sphingosine derivatives is described. l -Serine-derived aldehyde (Garner's aldehyde) ( 2 ) was treated with 1-alkenyl-zirconocene chlorides ( 3 ) in the presence of ZnBr 2 in THF to give the natural erythro -( anti -) isomers with high diastereoselectivity ( anti / syn =12–20:1). In contrast, reaction of 2 with 1-alkenyl-ethyl-zinc, prepared from 3 and Et 2 Zn, in CH 2 Cl 2 gave the unnatural threo -( syn -) isomers predominantly ( anti / syn =1:12–15).