STEREOCONTROL BY DIETHYLALUMINUM CHLORIDE IN THE ADDITION OF 2-LITHIOFURAN AND N-METHYL-2-LITHIOIMIDAZOLE TO ALPHA-ALKOXY NITRONES - TOTAL SYNTHESIS OF 5-O-CARBAMOYLPOLYOXAMIC ACID

Authors
DONDONI A FRANCO S MERCHAN FL MERINO P TEJERO T
Citation
A. Dondoni et al., STEREOCONTROL BY DIETHYLALUMINUM CHLORIDE IN THE ADDITION OF 2-LITHIOFURAN AND N-METHYL-2-LITHIOIMIDAZOLE TO ALPHA-ALKOXY NITRONES - TOTAL SYNTHESIS OF 5-O-CARBAMOYLPOLYOXAMIC ACID, Tetrahedron letters, 34(34), 1993, pp. 5479-5482
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
34
Issue
34
Year of publication
1993
Pages
5479 - 5482
Database
ISI
SICI code
0040-4039(1993)34:34<5479:SBDCIT>2.0.ZU;2-O
Abstract
The addition of the title metalated heterocycles 1 to the nitrone 2 de rived from D-glyceraldehyde acetonide leads to the corresponding syn-a dducts as major products (ds 88-96 %) while the reaction in the presen ce of Et2AlCl leads to anti isomers (ds 79-95 %); the synthesis of 5-O -carbamoylpolyoxamic acid from 4-O-benzyl-2,3-O-isopropylidene-L-threo se via the nitrone-furan adduct is described