Volume 31, Issue 23
Isocyclic Compounds
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ChemInform Abstract: Enantioselective Allylic Substitution Catalyzed by an Iridium Complex: Remarkable Effects of the Counter Cation.

Kaoru Fuji

Kaoru Fuji

Inst. Chem. Res., Kyoto Univ., Uji, Kyoto 611, Japan

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Naosumi Kinoshita

Naosumi Kinoshita

Inst. Chem. Res., Kyoto Univ., Uji, Kyoto 611, Japan

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Kiyoshi Tanaka

Kiyoshi Tanaka

Inst. Chem. Res., Kyoto Univ., Uji, Kyoto 611, Japan

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Takeo Kawabata

Takeo Kawabata

Inst. Chem. Res., Kyoto Univ., Uji, Kyoto 611, Japan

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First published: 08 June 2010

Abstract

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ChemInform Abstract

Allylic alkylation reactions of (I) and (V), catalyzed by an iridium complex of chiral aryl phosphites, are investigated. Nucleophilic attack anti to the phosphite ligand leads to the predominant formation of (S)-(III) using lithium and/or zinc as the counter cation. Harder anions favor the formation of (R)-(III). The enantiomeric excess of (S)-(III) is remarkably increased when a combination of lithium and zinc is used as counter cation, cf. (V)→(S)-(III).

chemical structure image

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