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Cover Feature: Tsuji–Trost Reaction of Non‐Derivatized Allylic Alcohols (Chem. Eur. J. 14/2018)
Chemistry - A European Journal ( IF 3.9 ) Pub Date : 2018-01-17 , DOI: 10.1002/chem.201705890 Sunisa Akkarasamiyo 1 , Supaporn Sawadjoon 1 , Andreas Orthaber 2 , Joseph S. M. Samec 1
Chemistry - A European Journal ( IF 3.9 ) Pub Date : 2018-01-17 , DOI: 10.1002/chem.201705890 Sunisa Akkarasamiyo 1 , Supaporn Sawadjoon 1 , Andreas Orthaber 2 , Joseph S. M. Samec 1
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Pd[κ2‐BiPhePhos][η3‐C3H5][OTf] is reported as an efficient catalyst in the Tsuji–Trost reaction of non‐derivatized allylic alcohols. Both inter‐ and intramolecular stereospecific allylic substitutions with various types of nucleophiles (C‐, S‐, N‐, and O‐centered) were successfully transformed. The desired products were obtained in high yield and high enantiospecificity and the only by‐product was water. The catalyst complexes were also studied and a pivotal effect of a counter ion was found where the chloride promotes decoordination of one of the phosphites that gets oxidized and this leads to decomposition of the catalyst. Application of this robust catalytic system in the total syntheses of bioactive natural products (S)‐cuspareine and (+)‐lentiginosine is demonstrated. More information can be found in the Full Paper by A. Orthaber, J. S. M. Samec et al. on page 3488.
中文翻译：
封面人物：未衍生的烯丙基醇的Tsuji-Trost反应（Eur。J. 14/2018）
PD [κ 2 -BiPhePhos] [η 3 -C 3 H ^ 5 ] [光学传递函数]据报道在非衍生化烯丙基醇的Tsuji-Trost反应中是一种有效的催化剂。分子间和分子内立体特异性烯丙基取代被各种类型的亲核试剂（以C，S，N和O为中心）成功转化。所需产物以高收率和高对映体特异性获得，唯一的副产物是水。还研究了催化剂配合物，发现了抗衡离子的枢转作用，其中氯化物促进了被氧化的亚磷酸酯之一的解配位，从而导致催化剂分解。这种强大的催化体系在生物活性天然产物（S的全部合成）中的应用）-cuspareine和（+）-lentiginosine已被证明。可以在A.Orthaber，J.S.M.Samec等人的论文全文中找到更多信息。在第3488页。
更新日期：2018-01-17
中文翻译：
封面人物：未衍生的烯丙基醇的Tsuji-Trost反应（Eur。J. 14/2018）
PD [κ 2 -BiPhePhos] [η 3 -C 3 H ^ 5 ] [光学传递函数]据报道在非衍生化烯丙基醇的Tsuji-Trost反应中是一种有效的催化剂。分子间和分子内立体特异性烯丙基取代被各种类型的亲核试剂（以C，S，N和O为中心）成功转化。所需产物以高收率和高对映体特异性获得，唯一的副产物是水。还研究了催化剂配合物，发现了抗衡离子的枢转作用，其中氯化物促进了被氧化的亚磷酸酯之一的解配位，从而导致催化剂分解。这种强大的催化体系在生物活性天然产物（S的全部合成）中的应用）-cuspareine和（+）-lentiginosine已被证明。可以在A.Orthaber，J.S.M.Samec等人的论文全文中找到更多信息。在第3488页。
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