Regioselective ring cleavage of chiral beta-trichloromethyl-beta-propiolactone with organoaluminum compounds for the synthesis of optically active intermediates

Authors
Fujisawa, T Ito, T Nishiura, S Shimizu, M
Citation
T. Fujisawa et al., Regioselective ring cleavage of chiral beta-trichloromethyl-beta-propiolactone with organoaluminum compounds for the synthesis of optically active intermediates, TETRAHEDR L, 39(52), 1998, pp. 9735-9738
Citations number
25
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
39
Issue
52
Year of publication
1998
Pages
9735 - 9738
Database
ISI
SICI code
0040-4039(199812)39:52<9735:RRCOCB>2.0.ZU;2-H
Abstract
A novel alkylating ring cleavage reaction of enantiomerically pure beta-tri chloromethyl-beta-propiolactone as a chiral building block with organoalumi num compounds provided ring-opened products with a chiral trichloromethyl c arbinol moiety. A product was demonstrated to be used as an effective chira l synthon for the synthesis of chiral bioactive derivatives such as ipsdien ol and sodium cilastatin. (C) 1998 Elsevier Science Ltd. All rights reserve d.