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Cyclizations of Silyl Enol Ether Radical Cations − The Cause of the Stereoselectivity
Author(s) -
Bunte Jens O.,
Heilmann Eike K.,
Hein Birka,
Mattay Jochen
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400128
Subject(s) - chemistry , silyl enol ether , enol , silylation , stereoselectivity , enol ether , selectivity , density functional theory , radical cyclization , photoinduced electron transfer , electron transfer , ether , reactive intermediate , photochemistry , medicinal chemistry , computational chemistry , organic chemistry , catalysis
We have used photoinduced electron transfer (PET) activation of silyl enol ethers for the synthesis of tricyclic hydrocarbons. The mechanism of this reaction was investigated by conducting independent radical‐induced cyclizations of corresponding iodo ketones and performing density functional theory (DFT) calculations on the possible intermediates. Our aim was to explain the nature of the reactive intermediate of the cyclization step and to find the causes of the various types of selectivity observed in this process. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)