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Volumn 46, Issue 48, 2007, Pages 9331-9334

Enantioselective preparation of 1,1-diarylethanes: Aldehydes as removable steering groups for asymmetric synthesis

Author keywords

Asymmetric synthesis; Cleavage reactions; Decarbonylation; Diarylethanes; Synthesis design

Indexed keywords

ALDEHYDES; CARBONYLATION; CHEMICAL ANALYSIS; PARAFFINS; SYNTHESIS (CHEMICAL);

EID: 37349031135     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200702995     Document Type: Article
Times cited : (108)

References (41)
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    • Recent progress in the metal-catalyzed hydroarylation of styrene derivatives has allowed access to 1,1-diarylalkanes in racemic form, see, for example: a H.-B. Sun, B. Li, R. Hua, Y. Yin, Chem. 2006, 4231;
    • Recent progress in the metal-catalyzed hydroarylation of styrene derivatives has allowed access to 1,1-diarylalkanes in racemic form, see, for example: a) H.-B. Sun, B. Li, R. Hua, Y. Yin, Eur. J. Org. Chem. 2006, 4231;
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    • For the gold standard in the asymmetric reduction of unfunctionalized C=C bonds, see: a S. Bell, B. Wuestenberg, S. Kaiser, F. Menges, A. Pfaltz. Science 2006, 311, 5761;
    • For the "gold standard" in the asymmetric reduction of unfunctionalized C=C bonds, see: a) S. Bell, B. Wuestenberg, S. Kaiser, F. Menges, A. Pfaltz. Science 2006, 311, 5761;
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    • and references therein
    • b) S. J. Roseblade, A. Pfaltz, C. R. Chim. 2007, 10, 178, and references therein.
    • (2007) C. R. Chim , vol.10 , pp. 178
    • Roseblade, S.J.1    Pfaltz, A.2
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    • 37349059139 scopus 로고    scopus 로고
    • The optically active diene ligand, [(1R,4R,8R)-5- benzyl-8-methoxy-1,8-dimethyl-2-(2′-methylpropyl)bicyclo[2.2.2]octa-2, 5-diene] and its enantiomer are commercially available from Aldrich under the name dolefin.
    • The optically active diene ligand, [(1R,4R,8R)-5- benzyl-8-methoxy-1,8-dimethyl-2-(2′-methylpropyl)bicyclo[2.2.2]octa-2, 5-diene] and its enantiomer are commercially available from Aldrich under the name "dolefin".
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    • For a recent review of Pd-catalyzed decarbonylations, see:, Ed, E. Negishi, Wiley, New York
    • For a recent review of Pd-catalyzed decarbonylations, see: J. Tsuji in Handbook of Organopalladium Chemistry for Organic Synthesis (Ed.: E. Negishi), Wiley, New York, 2002.
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    • For examples of recent applications of Ir-catalyzed decarbonylations, see: a F. Y. Kwong, H. W. Lee, W. H. Lam, L. Qiu, A. S. C. Chan, Tetrahedron: Asymmetry 2006, 17, 1238;
    • For examples of recent applications of Ir-catalyzed decarbonylations, see: a) F. Y. Kwong, H. W. Lee, W. H. Lam, L. Qiu, A. S. C. Chan, Tetrahedron: Asymmetry 2006, 17, 1238;
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    • For examples of Rh-catalyzed decarbonylation methods, see: a C. M. Beck, S. E. Rathmill, Y. J. Park, J. Chen, R. H. Crabtree, L. M. Liable-Sands, A. L. Rheingold, Organometallics 1999, 18, 5311;
    • For examples of Rh-catalyzed decarbonylation methods, see: a) C. M. Beck, S. E. Rathmill, Y. J. Park, J. Chen, R. H. Crabtree, L. M. Liable-Sands, A. L. Rheingold, Organometallics 1999, 18, 5311;
  • 33
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    • The optically active aldehydes 1a, 1b, 1d, and 1g have been prepared previously. For corresponding ee values and experimental data, see reference [9]. In all other cases, see the Supporting Information.
    • The optically active aldehydes 1a, 1b, 1d, and 1g have been prepared previously. For corresponding ee values and experimental data, see reference [9]. In all other cases, see the Supporting Information.
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    • 1H NMR spectra of the crude reaction mixtures.
    • 1H NMR spectra of the crude reaction mixtures.
  • 35
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    • It was found that stringent removal of methanol was necessary to minimize the oxidative Tishchenko-like coupling of the alcohol and the intermediate aldehyde 1a, generating methyl ester by-products
    • It was found that stringent removal of methanol was necessary to minimize the oxidative Tishchenko-like coupling of the alcohol and the intermediate aldehyde 1a, generating methyl ester by-products.
  • 40
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    • The reaction was performed with (+)-dolefin ligand [(1R,4R, 8R)-5-benzyl-8-methoxy-1,8-dimethyl-2-(2′-methyl-propyl)-bicyclo[2. 2.2]octa-2,5-diene].
    • The reaction was performed with (+)-dolefin ligand [(1R,4R, 8R)-5-benzyl-8-methoxy-1,8-dimethyl-2-(2′-methyl-propyl)-bicyclo[2. 2.2]octa-2,5-diene].
  • 41
    • 37349002257 scopus 로고    scopus 로고
    • The reaction was performed with epi-(-)-dolefin ligand [(1S,4S,8R)-5-benzyl-8-methoxy-1,8-dimethyl-2-(2′- methyl-propyl)-bicyclo[2.2.2]octa-2,5-diene].
    • The reaction was performed with epi-(-)-dolefin ligand [(1S,4S,8R)-5-benzyl-8-methoxy-1,8-dimethyl-2-(2′- methyl-propyl)-bicyclo[2.2.2]octa-2,5-diene].


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.