Enantioselective radical-mediated reduction of alpha-alkyl-alpha-iododihydrocoumarins in the presence of a chiral magnesium iodide

Authors
Murakata, M Tsutsui, H Takeuchi, N Hoshino, O
Citation
M. Murakata et al., Enantioselective radical-mediated reduction of alpha-alkyl-alpha-iododihydrocoumarins in the presence of a chiral magnesium iodide, TETRAHEDRON, 55(34), 1999, pp. 10295-10304
Citations number
32
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
34
Year of publication
1999
Pages
10295 - 10304
Database
ISI
SICI code
0040-4020(19990820)55:34<10295:ERROA>2.0.ZU;2-A
Abstract
An enantioselective reduction of alpha-allcyl-alpha-iododihydrocoumarins 1 by radical-mediated reactions using magnesium iodide and a chiral diamine 2 is described. The reactions of 1 with tributyltin hydride or triphenyltin hydride in the presence of a chiral Lewis acid generated from magnesium iod ide and 2 at -78 degrees C in ether-CH2Cl2 took place to afford reduced pro ducts 3. The determination of the absolute configurations of 3b-3d by chemi cal correlation with 3a is also described. (C) 1999 Elsevier Science Ltd. A ll rights reserved.