Ruthenium-Catalyzed Asymmetric Dehydrative Allylic Cyclization of Five-Membered Chalcogen Heteroaromatics

Shinji Tanaka; Shoutaro Iwase; Sena Kanda; Marie Kato; Yutaro Kiriyama; Masato Kitamura

doi:10.1055/a-1523-6826

Synthesis, Inhaltsverzeichnis

Synthesis 2021; 53(17): 3121-3125
DOI: 10.1055/a-1523-6826

special topic

Bond Activation – in Honor of Prof. Shinji Murai

Ruthenium-Catalyzed Asymmetric Dehydrative Allylic Cyclization of Five-Membered Chalcogen Heteroaromatics

Shinji Tanaka∗

^aResearch Center for Materials Science, Nagoya University, Chikusa, Nagoya 464-8602, Japan

,

Shoutaro Iwase

^bGraduate School of Pharmaceutical Sciences, Nagoya University, Chikusa, Nagoya 464-8601, Japan

,

Sena Kanda

^cDepartment of Chemistry, Nagoya University, Chikusa, Nagoya 464-8601, Japan

,

Marie Kato

^bGraduate School of Pharmaceutical Sciences, Nagoya University, Chikusa, Nagoya 464-8601, Japan

,

Yutaro Kiriyama

^cDepartment of Chemistry, Nagoya University, Chikusa, Nagoya 464-8601, Japan

,

Masato Kitamura∗

^bGraduate School of Pharmaceutical Sciences, Nagoya University, Chikusa, Nagoya 464-8601, Japan

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Abstract

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Abstract

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 σ-allyl complex.

Keywords

furan - thiophene - dehydrative allylation - ruthenium - asymmetric reaction

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Referenzen

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Zusatzmaterial

Supporting Information