NEW EXPEDIENT ROUTE TO THE STEREOSELECTIVE SYNTHESIS OF FLUORINATED 1,3-DIOL DERIVATIVES VIA ALUMINUM ACETALS DERIVED FROM BETA-ALKOXY ESTERS AND DIBAL

Authors
ISHIHARA T TAKAHASHI A HAYASHI H YAMANAKA H KUBOTA T
Citation
T. Ishihara et al., NEW EXPEDIENT ROUTE TO THE STEREOSELECTIVE SYNTHESIS OF FLUORINATED 1,3-DIOL DERIVATIVES VIA ALUMINUM ACETALS DERIVED FROM BETA-ALKOXY ESTERS AND DIBAL, Tetrahedron letters, 39(26), 1998, pp. 4691-4694
Citations number
17
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
26
Year of publication
1998
Pages
4691 - 4694
Database
ISI
SICI code
0040-4039(1998)39:26<4691:NERTTS>2.0.ZU;2-#
Abstract
On treating the aluminum acetal intermediates, generated in situ from ethyl 3-benzyloxy-2,2-difluoroalkanoates or 3-benzyloxy-4,4,4-trifluor obutanoate and diisobutylaluminum hydride at -78 degrees C for 1 h, wi th allylic stannanes in the presence of titanium(IV) dichloride diisop ropoxide at 0 degrees C for 8 h or at -30 degrees C for 6 h, the corre sponding allylated products, polyfluoro-1,3-diol derivatives, were obt ained in good yields with high anti stereoselectivity. (C) 1998 Elsevi er Science Ltd. All rights reserved.