Concise route to 3-arylisoquinoline skeleton by lewis acid catalyzed c(sp3)-h bond functionalization and its application to formal synthesis of (±)-Tetrahydropalmatine
An expeditious route to furnish an isoquinoline skeleton via hydride shift mediated C-H bond functionalization was developed. In this process, an unusual [1,5]-H shift without the assistance of the adjacent heteroatom took place to produce tetrahydroisoquinoline derivatives in good to excellent chemical yields. The formal synthesis of (±)-tetrahydropalmatine was achieved by exploiting this new transformation.
Mori, Keiji,Kawasaki, Taro,Akiyama, Takahiko
p. 1436 - 1439
(2012/05/05)
Rapid access to 3-aryltetralin skeleton via C(sp3)-H bond functionalization: Investigation on the substituent effect of aromatic ring adjacent to C-H bond in hydride shift/cyclization sequence
The concise construction of 3-aryltetralin skeleton via hydride shift mediated C-H bond functionalization was achieved. In this process, the benzylic [1,5]-H shift occurred smoothly to furnish tetralin derivatives in good to excellent chemical yields. The electronic and steric properties of the aromatic ring adjacent to the C-H bond influenced significantly the reactivity of this transformation.
Mori, Keiji,Sueoka, Shosaku,Akiyama, Takahiko
p. 1386 - 1388
(2012/01/12)
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