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Volumn 18, Issue 16, 2012, Pages 4844-4849

Catalytic enantiospecific [3+2] annulation of aminocyclopropanes with ketones

Author keywords

aminotetrahydrofuran; annulation; catalysis; D A aminocyclopropane; enantiospecificity; ketones

Indexed keywords

AMINOTETRAHYDROFURAN; ANNULATION; D-A AMINOCYCLOPROPANE; DIASTEREO-SELECTIVITY; DONOR-ACCEPTORS; ENANTIOSPECIFIC; ENANTIOSPECIFICITY; HIGH YIELD; TIN CHLORIDES;

EID: 84859575449     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201103971     Document Type: Article
Times cited : (94)

References (57)
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    • A reviewer proposed the use of the term [3+2] cycloaddition for this type of reaction because it is more precise than annulation, and could be in agreement with the IUPAC definition for cycloaddition: "A reaction in which two or more unsaturated molecules (or parts of the same molecule) combine with the formation of a cyclic adduct in which there is a net reduction of the bond multiplicity." Nevertheless, other authors do not agree that cycloaddition is completely correct in this case (see reference [2b]). According to a seminal publication by Huisgen, "Cycloaddition reactions do not involve the cleavage of sigma bonds" (rule 3)
    • O. A. Ivanova, E. M. Budynina, A. O. Chagarovskiy, I. V. Trushkov, M. Y. Melnikov, J. Org. Chem. 2011, 76, 8852-8868. A reviewer proposed the use of the term [3+2] cycloaddition for this type of reaction because it is more precise than annulation, and could be in agreement with the IUPAC definition for cycloaddition: "A reaction in which two or more unsaturated molecules (or parts of the same molecule) combine with the formation of a cyclic adduct in which there is a net reduction of the bond multiplicity." Nevertheless, other authors do not agree that cycloaddition is completely correct in this case (see reference [2b]). According to a seminal publication by Huisgen, "Cycloaddition reactions do not involve the cleavage of sigma bonds" (rule 3)
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    • In view of this controversy, we kept the term annulation throughout our publication, as it is accepted as correct by all scientists in the field. We let the reader make his own choice if he prefers to use the word cycloaddition
    • Angew. Chem. Int. Ed. Engl. 1968, 7, 321-328. In view of this controversy, we kept the term annulation throughout our publication, as it is accepted as correct by all scientists in the field. We let the reader make his own choice if he prefers to use the word cycloaddition.
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    • with aldehydes, see
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    • A 2-aminoTHF substructure search on the PubChem. Compound database gave >164000 entries for compounds with tertiary C5 atoms (3299 active in bioassays), and 3 entries for those with quaternary C5 atoms. For the PubChem. Compound database, see:, in, American Chemical Society, Washington
    • A 2-aminoTHF substructure search on the PubChem. Compound database gave >164000 entries for compounds with tertiary C5 atoms (3299 active in bioassays), and 3 entries for those with quaternary C5 atoms. For the PubChem. Compound database, see:, E. Bolton, Y. Wang, P. A. Thiessen, S. H. Bryant, in Annual Reports in Computational Chemistry, Vol. 4, American Chemical Society, Washington, 2008.
    • (2008) Annual Reports in Computational Chemistry, Vol. 4
    • Bolton, E.1    Wang, Y.2    Thiessen, P.A.3    Bryant, S.H.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.