铁催化的普林斯-彼得森反应直接合成Δ-2,7-二取代氧杂环庚三烯
Iron-Catalyzed Prins-Peterson Reaction for the Direct Synthesis of Δ-2,7-Disubstituted Oxepenes.
作者信息
Cruz Daniel A, Sinka Victoria, Martín Víctor S, Padrón Juan I
机构信息
Instituto Universitario de Bio-Orgánica "Antonio González" (CIBICAN), "Síntesis Orgánica Sostenible, Unidad Asociada al CSIC", Departamento de Química Orgánica , Universidad de La Laguna , C/Francisco Sánchez 2 , San Cristóbal de La Laguna , Santa Cruz de Tenerife 38206 , Spain.
Instituto de Productos Naturales y Agrobiología, Consejo Superior de Investigaciones Científicas (IPNA-CSIC) , Avda. Astrofísico Francisco Sánchez 3 , San Cristóbal de La Laguna , Santa Cruz de Tenerife 38206 , Spain.
出版信息
J Org Chem. 2018 Oct 19;83(20):12632-12647. doi: 10.1021/acs.joc.8b01978. Epub 2018 Oct 5.
A direct iron(III)-catalyzed Prins-Peterson reaction involving α-substituted γ-triphenylsilyl bis-homoallylic alcohols and aldehydes is described. Thus, cis-Δ-2,7-disubstituted oxepenes were synthesized in a diastereoselective reaction using sustainable catalytic conditions (3-5 mol %). This highly productive process is the result of a cascade of three chemical events with the concomitant formation of a C-O bond, a C-C bond, and a Δ endocyclic double bond, through a Prins cyclization followed by a Peterson-type elimination. This tandem reaction is chemoselective vs the classical Prins cyclization.
描述了一种直接的铁（III）催化的普林斯-彼得森反应，该反应涉及α-取代的γ-三苯基甲硅烷基双高烯丙醇和醛。因此，在可持续的催化条件（3-5摩尔%）下，通过非对映选择性反应合成了顺式-Δ-2,7-二取代氧杂环庚三烯。这个高产率的过程是三个化学事件级联的结果，伴随着通过普林斯环化然后是彼得森型消除形成一个C-O键、一个C-C键和一个Δ内双键。与经典的普林斯环化相比，这种串联反应具有化学选择性。
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