STEREOSELECTIVE RADICAL ALLYLATIONS OF ALPHA-IODO-BETA-ALKOXY ESTERS - REVERSAL OF FACIAL SELECTIVITY BY LEWIS-ACID COMPLEXATION

Authors
GUINDON Y GUERIN B CHABOT C MACKINTOSH N OGILVIE WW
Citation
Y. Guindon et al., STEREOSELECTIVE RADICAL ALLYLATIONS OF ALPHA-IODO-BETA-ALKOXY ESTERS - REVERSAL OF FACIAL SELECTIVITY BY LEWIS-ACID COMPLEXATION, Synlett, (5), 1995, pp. 449-451
Citations number
36
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synlett → ACNP
ISSN journal
09365214
Issue
5
Year of publication
1995
Pages
449 - 451
Database
ISI
SICI code
0936-5214(1995):5<449:SRAOAE>2.0.ZU;2-1
Abstract
The radical allylation of a series of a-iodo-P-alkoxy eaters under bid entate chelation-controlled conditions is reported and compared with t he analogous reactions under non-chelating conditions. The addition of MgB2 . OEt(2) is shown to give excellent selectivity for the anti pro ducts, in some cases ratios greater than 100 : 1 are obtained. The rea ctions require initiation with Et(3)B and can be inhibited by m- and p -dinitrobenzene, implying a radical based mechanism. Iodides, bromides and phenyl selenides all are suitable substrates.