CONCISE ASYMMETRIC ROUTES TO 2,2,4-TRISUBSTITUTED TETRAHYDROFURANS VIA CHIRAL TITANIUM IMIDE ENOLATES - KEY INTERMEDIATES TOWARDS SYNTHESISOF HIGHLY-ACTIVE AZOLE ANTIFUNGALS SCH-51048 AND SCH-56592

Authors
SAKSENA AK GIRIJAVALLABHAN VM WANG HY LIU YT PIKE RE GANGULY AK
Citation
Ak. Saksena et al., CONCISE ASYMMETRIC ROUTES TO 2,2,4-TRISUBSTITUTED TETRAHYDROFURANS VIA CHIRAL TITANIUM IMIDE ENOLATES - KEY INTERMEDIATES TOWARDS SYNTHESISOF HIGHLY-ACTIVE AZOLE ANTIFUNGALS SCH-51048 AND SCH-56592, Tetrahedron letters, 37(32), 1996, pp. 5657-5660
Citations number
9
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
32
Year of publication
1996
Pages
5657 - 5660
Database
ISI
SICI code
0040-4039(1996)37:32<5657:CART2T>2.0.ZU;2-V
Abstract
Two complimentary approaches to the key (-)-(2R)-cis-tosylate 1 and it s (+)-(2S)-enantiomer 15 via generation of chiral imide enolates havin g a 2,2-disubstituted olefin functionality in the P-position, are desc ribed. In a ''protecting group free'' sequence, reaction of the titani um enolate generated from (4R)-benzyl-2-oxazolidinone derived imide 5b with s-trioxane provided a convenient intermediate 19 which could be directly subjected to 2,4-diastereoselective iodocyclization. Copyrigh t (C) 1996 Elsevier Science Ltd