The first catalytic enantioselective Nozaki-Hiyama reaction

Angewandte Chemie - International Edition

Volumn 38, Issue 22, 1999, Pages 3357-3359

  Bandini, Marco ^a   Cozzi, Pier Giorgio ^a   Melchiorre, Paolo ^a   Umani Ronchi, Achille ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

Aldehydes; Asymmetric catalysis; Chromium; Redox chemistry; Schiff bases

Indexed keywords

ALDEHYDE; CHROMIUM; MANGANESE; SCHIFF BASE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; COMPLEX FORMATION; ENANTIOMER; OXIDATION REDUCTION REACTION; REACTION ANALYSIS; STEREOCHEMISTRY; STOICHIOMETRY;

EID: 0033571364     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19991115)38:22<3357::AID-ANIE3357>3.0.CO;2-W     Document Type: Article

References (34)

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22. III(salen)] complexes in asymmetric catalysis see: a) L. E. Martínoz, J. L. Leighton, D. H. Carsten, E. N. Jacobsen, J. Am. Chem. Soc. 1995, 117, 5897-5898;
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27. Chiral ligands such as bishydrooxazoles, 2,2′-dihydroxy-1,1′-biphenyl (BINOL). α,α,α′,α′-tetraaryl-1,3-dioxolane-4,5- dimethanol (TAD-DOL), sulfonamides, amino alcohols, and phosphanes afforded the homoallylic alcohol in racemic form.
28. Bases such as pyridine and N-methyl imidazolo were screened as well, but in these cases the homoallylic alcohol was isolated in very low yields, probably due to a complexation of the Cr species by the bases.
29. The use of [Cr(salen)] complex following Jacobsen's protocol in the addition of allyl bromide to benraldehyde afforded the desired homoallylic alcohol in 52% yield and 38% ee.
30. 2Cl in the allylation of the benzaldehyde we obtained 76% ee and 78% ee, respectively.
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33. 111(salen)] complexes and related mechanistic studies were reported by Jacobsen et al. At the present, we are not able to suggest any intermediate for our reaction. However, the observed configuration of the homoallylic alcohol might derive from a mechanism involving cooperative intramolecular dimetallic catalysis: see K. B. Hansen, J. E. Leighton, E. N. Jacobsen, J. Am. Chem. Soc. 1996, 118, 10924-10925; R. G. Konsler, J. Karl, E. N. Jacobsen, J. Am. Chem. Soc. 1998, 120, 10780-10781.
34. 111(salen)] complexes and related mechanistic studies were reported by Jacobsen et al. At the present, we are not able to suggest any intermediate for our reaction. However, the observed configuration of the homoallylic alcohol might derive from a mechanism involving cooperative intramolecular dimetallic catalysis: see K. B. Hansen, J. E. Leighton, E. N. Jacobsen, J. Am. Chem. Soc. 1996, 118, 10924-10925; R. G. Konsler, J. Karl, E. N. Jacobsen, J. Am. Chem. Soc. 1998, 120, 10780-10781.