Chiral Olefins as steering ligands: Syntheses of C-1-symmetric dibenzoa,ecyclooctenes ((R)dbcot)

Lang  F; Breher  F; Stein  DGrutzmacher  H

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Chiral Olefins as steering ligands: Syntheses of C-1-symmetric dibenzoa,ecyclooctenes ((R)dbcot)

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A simple three-step synthesis of chiral dibenzoa,ecyclooctenes (dbcot) starting from commercially available dibenzosuberenone was developed. These compounds give highly stable and robust rhodium(I) and iridium(I) diene complexes of the type M((R)dbcot)(L-1)(L-2) (M = Rh, Ir; L-1, L-2 = MeCN, Cl, diamine, chloride). The complex Rh((R)-(Ph)dbcot)((R)-(+)-1,1'-binaphthyl-2,2'-diamine)+OTf- could be obtained in enantiomerically pure form and catalyzes the enantioselective 1,2-addition of PhB(OH)(2) to alpha,beta-unsaturated ketones with good activity and acceptable enantiomeric excess (62). The iridium complex Ir((Ph)dbcot)-(MeCN)(2)+OTf- catalyzes the hydrogenation of dimethylitaconate with good activity, while the rhodium complexes are almost inactive. Likewise, the complex Ir((Ph)dbcot)(H2NCH2-CH2NH2)+OTf- serves as a rather efficient catalyst precursor with an activity 4 orders of magnitude higher than for the analogous rhodium complex. These experiments further establish the use of dienes as steering ligands in catalysis.

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《Organometallics》 |2005年第12期|2997-3007|共11页
作者
Lang F; Breher F; Stein DGrutzmacher H;
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ETH, Dept Chem & Appl Biosci, CH-8093 Zurich, Switzerland;

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正文语种英语
中图分类有机化学;
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CATALYZED ASYMMETRIC 1; 4-ADDITION; CARBONYL-COMPOUNDS; EFFICIENT SYNTHESIS; CRYSTAL-STRUCTURE; RING INVERSION; COMPLEXES; HYDROGENATION; REDUCTION; CHLORIDE; DIBENZOA; ECYCLOOCTATETRAENE;

Chiral Olefins as steering ligands: Syntheses of C-1-symmetric dibenzoa,ecyclooctenes ((R)dbcot)

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