ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The stereoselectivity of radical reactions using cyclic iodohydrins and 2-alkoxy iodides was investigated on a simple model system obtained from indene (see 1a-d). The low level of stereoselectivity inherent to this type of systems could neither be overcome by using large protective group on the O-atom of 1c nor by complexation with Lewis acids. However, starting from the free alcohol 1c, it was possible to obtain very high selectivities (trans/cis 〉 100:1) by forming an aluminium alkoxide derivative upon treatment with methylaluminium bis[2,6-di(tert-butyl)-4-methylphenoxide] (MAD) before running the radical reaction. Despite the high steric demand of these complexes, the reactions gave satisfactory yields even for the formation of C—C bonds.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19950780421
