Solid-Supported Nitroso Hetero Diels–Alder Reactions. 2. Arylnitroso Dienophiles: Scope and Limitations

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• 作者：Viktor Krchň ; á ; k ; Ute Moellmann ; Hans-Martin Dahse ; Marvin J. Miller
• 刊名：Journal of Combinatorial Chemistry
• 出版年：2008
• 出版时间：January 2008
• 年：2008
• 卷：10
• 期：1
• 页码：104 - 111
• 全文大小：601K
• 年卷期：v.10,no.1(January 2008)
• ISSN：1520-4774

文摘

Immobilized arylnitroso dienophiles were prepared and used in hetero Diels–Alder (HDA) reactions with a variety of dienes. Polymer-supported arylnitroso species were prepared on several linkers cleavable by different cleavage reagents and used for (i) optimization of reaction conditions for HDA reactions, (ii) evaluation of the reaction outcome with various dienes, (iii) comparison of relative reactivities of dienes, and (iv) assessment of the stability of HDA adducts toward cleavage conditions typically used in solid-phase preparation (TFA). The outcome of the HDA reactions has been evaluated for a set of 19 dienes, and the relative reactivities of dienes that yielded the expected HDA adducts were compared. Cleaved products were submitted to biological assays, and the results are reported.