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Volumn 46, Issue 20, 2007, Pages 3701-3705

Enantioselective alkylation of acyclic α,α-disubstituted tributyltin enolates catalyzed by a {Cr(salen)} complex

Author keywords

Alkylation; Asymmetric catalysis; Chromium; Enolates; N,O ligands

Indexed keywords

ALKYLATION; AMINES; CATALYSIS; CHROMIUM COMPOUNDS; ENANTIOSELECTIVITY; ISOMERS;

EID: 34250891887     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200604901     Document Type: Article
Times cited : (89)

References (62)
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    • See the Supporting Information for details
    • See the Supporting Information for details.
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    • The para-siloxy salen ligands were prepared in three steps and in high overall yield (70-80%) from the commercially available tert- butylhydroquinone; see the Supporting Information for details.
    • The para-siloxy salen ligands were prepared in three steps and in high overall yield (70-80%) from the commercially available tert- butylhydroquinone; see the Supporting Information for details.
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    • Treatment of the [(salen)CrCl] complex 1b with NaI at room temperature resulted in the quantitative exchange of the counterion; see the Supporting Information for details
    • Treatment of the [(salen)CrCl] complex 1b with NaI at room temperature resulted in the quantitative exchange of the counterion; see the Supporting Information for details
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    • 13C NMR spectroscopy have been inconclusive.
    • 13C NMR spectroscopy have been inconclusive.
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    • J. E. Dubois, P. Felmann, Tetrahedron Lett. 1975, 16, 1225-1228. Assuming that the isomeric mixture of the tin enolates undergo alkylation with identical enantioselectivity, a maximum 9-fold difference in rate is necessary to explain the observed levels of enantioselectivity for the alkylation of a 1.5:1 mixture of E/Z tin enolates.
    • b) J. E. Dubois, P. Felmann, Tetrahedron Lett. 1975, 16, 1225-1228. Assuming that the isomeric mixture of the tin enolates undergo alkylation with identical enantioselectivity, a maximum 9-fold difference in rate is necessary to explain the observed levels of enantioselectivity for the alkylation of a 1.5:1 mixture of E/Z tin enolates.


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