Enantioselective Allylic Substitution of Cinnamyl Esters Catalyzed by Iridium−Chiral Aryl Phosphite Complex:  Conspicuous Change in the Mechanistic Spectrum by a Countercation and Solvent

Enantioselective Allylic Substitution of Cinnamyl Esters Catalyzed by Iridium−Chiral Aryl Phosphite Complex:  Conspicuous Change in the Mechanistic Spectrum by a Countercation and Solvent

Iridium-catalyzed asymmetric allylic alkylation of monoaryl substrates 4−6 with chiral phosphites 1−3 has been investigated. Although branched isomers were formed with high regioselectivities, the enantioselectivities of these products were remarkably influenced by solvents, countercations, and addi...

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Veröffentlicht in:Journal of organic chemistry 2004-11, Vol.69 (23), p.7960-7964
Hauptverfasser: Kinoshita, Naosumi, Marx, Karsten H, Tanaka, Kiyoshi, Tsubaki, Kazunori, Kawabata, Takeo, Yoshikai, Naohiko, Nakamura, Eiichi, Fuji, Kaoru
Format: Artikel
Sprache:eng
Schlagworte:
Chemical reactivity
Chemistry
Exact sciences and technology
Organic chemistry
Reactivity and mechanisms
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Zusammenfassung:Iridium-catalyzed asymmetric allylic alkylation of monoaryl substrates 4−6 with chiral phosphites 1−3 has been investigated. Although branched isomers were formed with high regioselectivities, the enantioselectivities of these products were remarkably influenced by solvents, countercations, and additives (ZnCl2 and LiCl).
ISSN:0022-3263
1520-6904
DOI:10.1021/jo048834d