Proto- and iodo-lactonization reaction of substituted alpha,beta : gamma,delta-unsaturated carboxylic acid

Authors
Kuroda, C Tang, CY Tanabe, M Funakoshi, M
Citation
C. Kuroda et al., Proto- and iodo-lactonization reaction of substituted alpha,beta : gamma,delta-unsaturated carboxylic acid, B CHEM S J, 72(7), 1999, pp. 1583-1587
Citations number
29
Categorie Soggetti
Chemistry
Journal title
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
ISSN journal
00092673 → ACNP
Volume
72
Issue
7
Year of publication
1999
Pages
1583 - 1587
Database
ISI
SICI code
0009-2673(199907)72:7<1583:PAIROS>2.0.ZU;2-2
Abstract
Iodolactonization of 4,5-disubstituted 2-(trimethylsilylmethyl)- and 2-meth yl-penta-2,4-dienoic acids was studied. The latter afforded the correspondi ng iodolactone in good yield by treatment with I-2 in MeCN. Iodolactone was also obtained by treatment with I-2/NaHCO3/CHCl3/H2O in the presence of ce rium(IV) salt as an additive. It was found that protolactonization proceeds by the aid of the trimethylsilyl group, while it prevents iodolactonizatio n.