Catalyzed Asymmetric  DielsAlder  Reactions of Benzoquinone. Total Synthesis of (−)‐Ibogamine | Zendy

White James D. | Zendy; Choi Younggi | Zendy

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Catalyzed Asymmetric DielsAlder 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.

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