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Catalyzed Asymmetric DielsAlder Reactions of Benzoquinone. Total Synthesis of (−)-Ibogamine

✍ Scribed by James D. White; Younggi Choi

Book ID
102253496
Publisher
John Wiley and Sons
Year
2002
Tongue
German
Weight
254 KB
Volume
85
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The DielsAlder 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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ChemInform Abstract: Catalyzed Asymmetri
ChemInform Abstract: Catalyzed Asymmetric Diels—Alder Reaction of Benzoquinone. Total Synthesis of (-)-Ibogamine.
✍ James D. White; Younggi Choi 📂 Article 📅 2000 🏛 John Wiley and Sons ⚖ 29 KB 👁 1 views

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