DIASTEREOFACIAL SELECTIVITY OF RADICAL CYCLIZATION USING CHIRAL ALPHA,BETA-UNSATURATED ESTER AND AMIDE - INVESTIGATION OF A NEW CHIRAL SYNTHON SYNTHESIS

Authors
KATSUMATA A IWAKI T FUKUMOTO K IHARA M
Citation
A. Katsumata et al., DIASTEREOFACIAL SELECTIVITY OF RADICAL CYCLIZATION USING CHIRAL ALPHA,BETA-UNSATURATED ESTER AND AMIDE - INVESTIGATION OF A NEW CHIRAL SYNTHON SYNTHESIS, Heterocycles, 46, 1997, pp. 605-616
Citations number
24
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
46
Year of publication
1997
Pages
605 - 616
Database
ISI
SICI code
0385-5414(1997)46:<605:DSORCU>2.0.ZU;2-R
Abstract
The chiral alpha,beta-unsaturated ester (3a) gave cyclic acetal (4aA) in a highly diastereoselective manner (>98% de) by radical cyclization , which was carried out in the presence of MAD. Furthermore, 4aA was c onverted into chiral lactone (9), possessing the stereogenic center wi th three differentiated C-2 units.