Reductive radical cyclization of cyclic gamma-cyanoketones promoted by samarium(II) iodide without photoirradiation

Authors
Kakiuchi, K Fujioka, Y Yamamura, H Tsutsumi, K Morimoto, T Kurosawa, H
Citation
K. Kakiuchi et al., Reductive radical cyclization of cyclic gamma-cyanoketones promoted by samarium(II) iodide without photoirradiation, TETRAHEDR L, 42(43), 2001, pp. 7595-7598
Citations number
9
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
43
Year of publication
2001
Pages
7595 - 7598
Database
ISI
SICI code
0040-4039(20011022)42:43<7595:RRCOCG>2.0.ZU;2-B
Abstract
Reaction of cyclic gamma -cyanoketones with 3 equiv. of SmI2 in the presenc e of t-BuOH as a proton source in HMPA-THF without photoirradiation gave th e desired alpha -hydroxycycloalkanones along with overreduced ketones after hydrolysis. In the absence of t-BuOH, the formation of the overreduced ket ones was depressed and the yields of the a-hydroxyketones increased, while the reaction proceeded slowly. (C) 2001 Elsevier Science Ltd. All rights re served.