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Volumn 125, Issue 20, 2003, Pages 6200-6210

Molecular recognition of α,β-unsaturated carbonyl compounds using aluminum tris(2,6-diphenylphenoxide) (ATPH): Structural and conformational analysis of ATPH complexes and application to the selective vinylogous aldol reaction

Author keywords

[No Author keywords available]

Indexed keywords

ACIDS; CHEMICAL REACTIONS; OXYGEN; SUBSTRATES;

EID: 0038288697     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0205941     Document Type: Article
Times cited : (43)

References (82)
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    • n) with respect to the orientation of the α,βdouble bond. equation presented
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    • 1H NMR shifts exactly corresponding to 1:1 complexes between ATPH and carbonyl compounds. A slow exchange between free and bound substrates on a NMR time scale caused neither shifts of free carbonyl compounds nor average shifts between these substrates.
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    • In fact, a rapid equilibrium (s-trans ⇄ s-cis, for example, see Figure 6) faster than the rate of aldolization is envisioned by complete reversal of the olefin configuration (the E-γ-methyl of -15 was delivered to the Z-γ-methylene of 20).
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    • As one of the referees suggested, significant effects of the second equivalent of ATPH, which presumably activates the aldehyde partner, need further investigation. In the absence of the second ATPH, a considerable decrease in chemical yields was consistently observed.
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    • Compared directly with commercially available samples. Also see: Bobbitt, J. M. J. Org. Chem. 1998, 63, 9367.
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