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Catalyzed Asymmetric DielsAlder Reactions of Benzoquinone. Total Synthesis of (−)‐Ibogamine
Author(s) -
White James D.,
Choi Younggi
Publication year - 2002
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.200290014
Subject(s) - chemistry , diels–alder reaction , benzoquinone , yield (engineering) , enantiomer , diol , absolute configuration , enantioselective synthesis , total synthesis , catalysis , enantiomeric excess , stereochemistry , organic chemistry , medicinal chemistry , materials science , metallurgy
The DielsAlder reaction of 1,4‐benzoquinone with 1,3‐dienes catalyzed by Mikami 's [Ti{( S )‐binol(2−)}Cl 2 ] complex (binol=[1,1′‐binaphthalene]‐2,2′‐diol) gives cycloadducts in good yield and in high enantiomer excess. A model is proposed to explain the observed absolute configuration of cycloadducts, and the reaction is used as the key step in an asymmetric synthesis leading to the alkaloid (−)‐ibogamine.