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Volumn 66, Issue 16, 2010, Pages 2969-2980

α-Acyloxynitroso dienophiles in [4+2] hetero Diels-Alder cycloadditions: mechanistic insights

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA ACYCLOXYNITROSO DIENOPHILE DERIVATIVE; AMINOALCOHOL; LEWIS ACID; UNCLASSIFIED DRUG;

EID: 77949568646     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.02.065     Document Type: Article
Times cited : (16)

References (175)
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    • See also
    • See also:
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    • note
    • A significative increase in yield of the domino sequence has been obtained since the publication of our preliminary communication, from 41% to 54% (over three steps, average of 81% per step).
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    • note
    • The reaction of acetone oxime and cyclohexanone oxime with lead tetraacetate in dichloromethane afforded the corresponding α-acetoxynitroso derivatives in only 33 and 37% isolated yield. The residual acetic acid in lead tetraacetate led to considerable amount of hydrolysis of the α-acetoxynitroso moiety.
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    • Lead tetraacetate toxicity is a well established phenomena, for recent references, see
    • Lead tetraacetate toxicity is a well established phenomena, for recent references, see:
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    • 2O donor and as a base (see: To rule out any influence of the powdered 4 Å molecular sieves in yield variability, experiments were run in their absence. However, product distribution and yields were still highly variable with or without molecular sieves leading us to discard sieves as a major cause of non-reproducibility
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    • See Supporting data
    • See Supporting data.
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    • note
    • Experimentally, we have observed that dienophile 43 was much less stable than dienophile 32 in the presence of a Lewis acid or an aqueous HCl solution (1 N).
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    • note
    • The reported results indicate that the addition of Lewis acids decreases the rate of the cycloaddition reaction of α-acyloxynitroso derivatives. It is worth noting that the rate-determining step of this cycloaddition might not involve Lewis acid and that the observed low enantiomeric excess might be the result of an enantioselective Lewis acid opening of the cycloadduct. We wish to thank a reviewer for suggesting this possibility.
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    • For the General information, see Supporting data
    • For the General information, see Supporting data.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.