抄録
A chemoselective hydrogenation of isoquinoline carbocycles was achieved by using the catalyst prepared from Ru(methallyl)2(cod) and trans-chelate chiral ligand PhTRAP. The unique chemoselectivity achieved in this hydrogenation could be ascribed to the trans-chelation of the chiral ligand. The procedure for preparing the catalyst strongly affects the reproducibility of the carbocycle hydrogenation. Various 5-, 6-, 7-, and 8-substituted isoquinolines were selectively hydrogenated at their carbocycles to afford 5,6,7,8-tetrahydroisoquinolines as major products in high yields with moderate or good enantioselectivities. Some mechanistic studies suggested that the stereogenic center was created during the initial addition of H2 to the aromatic ring in the hydrogenation of 5-substituted isoquinolines. In other words, the stereochemical control was accompanied by the dearomatization.
| 元の言語 | 英語 |
|---|---|
| ページ（範囲） | 3829-3839 |
| ページ数 | 11 |
| ジャーナル | Journal of Organic Chemistry |
| 巻 | 83 |
| 発行部数 | 7 |
| DOI | |
| 出版物ステータス | 出版済み - 4 6 2018 |
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All Science Journal Classification (ASJC) codes
- Organic Chemistry
これを引用
Ruthenium-catalyzed chemo-and enantioselective hydrogenation of isoquinoline carbocycles. / Jin, Yushu; Makida, Yusuke; Uchida, Tatsuya; Kuwano, Ryoichi.
：: Journal of Organic Chemistry, 巻 83, 番号 7, 06.04.2018, p. 3829-3839.研究成果: ジャーナルへの寄稿 › 記事
}
TY - JOUR
T1 - Ruthenium-catalyzed chemo-and enantioselective hydrogenation of isoquinoline carbocycles
AU - Jin, Yushu
AU - Makida, Yusuke
AU - Uchida, Tatsuya
AU - Kuwano, Ryoichi
PY - 2018/4/6
Y1 - 2018/4/6
N2 - A chemoselective hydrogenation of isoquinoline carbocycles was achieved by using the catalyst prepared from Ru(methallyl)2(cod) and trans-chelate chiral ligand PhTRAP. The unique chemoselectivity achieved in this hydrogenation could be ascribed to the trans-chelation of the chiral ligand. The procedure for preparing the catalyst strongly affects the reproducibility of the carbocycle hydrogenation. Various 5-, 6-, 7-, and 8-substituted isoquinolines were selectively hydrogenated at their carbocycles to afford 5,6,7,8-tetrahydroisoquinolines as major products in high yields with moderate or good enantioselectivities. Some mechanistic studies suggested that the stereogenic center was created during the initial addition of H2 to the aromatic ring in the hydrogenation of 5-substituted isoquinolines. In other words, the stereochemical control was accompanied by the dearomatization.
AB - A chemoselective hydrogenation of isoquinoline carbocycles was achieved by using the catalyst prepared from Ru(methallyl)2(cod) and trans-chelate chiral ligand PhTRAP. The unique chemoselectivity achieved in this hydrogenation could be ascribed to the trans-chelation of the chiral ligand. The procedure for preparing the catalyst strongly affects the reproducibility of the carbocycle hydrogenation. Various 5-, 6-, 7-, and 8-substituted isoquinolines were selectively hydrogenated at their carbocycles to afford 5,6,7,8-tetrahydroisoquinolines as major products in high yields with moderate or good enantioselectivities. Some mechanistic studies suggested that the stereogenic center was created during the initial addition of H2 to the aromatic ring in the hydrogenation of 5-substituted isoquinolines. In other words, the stereochemical control was accompanied by the dearomatization.
UR - http://www.scopus.com/inward/record.url?scp=85045089078&partnerID=8YFLogxK
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U2 - 10.1021/acs.joc.8b00190
DO - 10.1021/acs.joc.8b00190
M3 - Article
AN - SCOPUS:85045089078
VL - 83
SP - 3829
EP - 3839
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 7
ER -