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Diastereoselective Radical Reactions Starting from Cyclic Iodohydrin Derivatives
Author(s) -
Moufid Nadira,
Renaud Philippe
Publication year - 1995
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19950780421
Subject(s) - chemistry , stereoselectivity , steric effects , indene , alkoxide , medicinal chemistry , carbon atom , alkoxy group , alcohol , lewis acids and bases , derivative (finance) , stereochemistry , organic chemistry , catalysis , ring (chemistry) , alkyl , financial economics , economics
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 CC bonds.