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Volumn 55, Issue 2, 2016, Pages 566-571

Practical Organocatalytic Synthesis of Functionalized Non-C2-Symmetrical Atropisomeric Biaryls

Author keywords

atropisomerism; biaryls; organocatalysis; rearrangements; synthetic methods

Indexed keywords

CATALYSIS;

EID: 84958741433     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201508419     Document Type: Article
Times cited : (103)

References (63)
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    • A great advantage of this approach is that in the case of the BINOL-type products the OH substituents in the 2- and 2′-positions are directly obtained in their unprotected form and no extra deprotection step is needed. If the biaryl product contains more than one protected OH group (i.e., OMe), selective deprotection of these groups becomes very challenging. Therefore it is desirable to have only the 2- and 2′-hydroxy groups in their unprotected form as it allows the most flexibility with regard to coordination with metals and further transformations (e.g., conversion of phosphoramidites and phosphoric acids).
    • A great advantage of this approach is that in the case of the BINOL-type products the OH substituents in the 2- and 2′-positions are directly obtained in their unprotected form and no extra deprotection step is needed. If the biaryl product contains more than one protected OH group (i.e., OMe), selective deprotection of these groups becomes very challenging. Therefore it is desirable to have only the 2- and 2′-hydroxy groups in their unprotected form as it allows the most flexibility with regard to coordination with metals and further transformations (e.g., conversion of phosphoramidites and phosphoric acids).
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    • A model system was used in which the methyl (Me) groups of the quinone monoacetal (1) were replaced with hydrogen (H) atoms.
    • A model system was used in which the methyl (Me) groups of the quinone monoacetal (1) were replaced with hydrogen (H) atoms.
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    • -1 error in the activation barrier for the uncatalyzed reaction. See.
    • -1 error in the activation barrier for the uncatalyzed reaction. See:, T. R. Ramadhar, R. A. Batey, Comput. Theor. Chem. 2011, 976, 167-182.
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    • Ramadhar, T.R.1    Batey, R.A.2
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    • We were unable to isolate mixed-acetal intermediates from the reaction mixtures. This is not surprising given the highly acid-sensitive nature of quinone monoacetals.
    • We were unable to isolate mixed-acetal intermediates from the reaction mixtures. This is not surprising given the highly acid-sensitive nature of quinone monoacetals.
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    • CCDC 1436770 (5 c) and 1436773 (5 s) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre.
    • CCDC 1436770 (5 c) and 1436773 (5 s) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.