Ruthenium-Catalyzed Asymmetric Dehydrative Allylic Cyclization of Five-Membered Chalcogen Heteroaromatics
Ruthenium-Catalyzed Asymmetric Dehydrative Allylic Cyclization of Five-Membered Chalcogen Heteroaromatics
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DOI：
10.1055/a-1523-6826
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发表时间：
2021-06-07
影响因子：
2.6
通讯作者：
Kitamura, Masato
中科院分区：
文献类型：
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作者：
Tanaka, Shinji;Iwase, Shoutaro;Kitamura, Masato
采用手性吡啶羧酸（Cl-Naph-PyCOOH）的阳离子环戊二烯钌（CpRu）配合物进行了呋喃和噻吩的不对称脱水分子内烯丙化反应。呋喃和噻吩与烯丙醇拴系在一起，使用0.1-5摩尔%的催化剂，生成相应的双环化合物，收率高，对映选择性高。我们发现该反应通过与我们之前报道的类似的对映面选择机制进行，除了生成中间的sigma-烯丙基络合物外，还包括卤素和氢键的形成。
The asymmetric dehydrative intramolecular allylation reactions of furan and thiophene were performed using a cationic cyclopentadienyl-ruthenium (CpRu) complex of a chiral pyridine carboxylic acid, namely Cl-Naph-PyCOOH. Both furan and thiophene tethered with an allylic alcohol gave the corresponding bicyclic compounds in high yields and enantioselectivities using 0.1-5 mol% of the catalyst. The reaction was found to proceed via a similar enantioface selection mechanism to that previously reported by our group, which involved halogen and hydrogen bond formation, in addition to the generation of an intermediate sigma-allyl complex.