130907-16-3Relevant academic research and scientific papers
Concise route to 3-arylisoquinoline skeleton by lewis acid catalyzed c(sp3)-h bond functionalization and its application to formal synthesis of (±)-Tetrahydropalmatine
Mori, Keiji,Kawasaki, Taro,Akiyama, Takahiko
, p. 1436 - 1439 (2012/05/05)
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.
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
Mori, Keiji,Sueoka, Shosaku,Akiyama, Takahiko
supporting information; experimental part, p. 1386 - 1388 (2012/01/12)
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.
Functionalization of Csp3-H bond-Sc(OTf)3-catalyzed domino 1,5-hydride shift/cyclization/Friedel-Crafts acylation reaction of benzylidene Meldrum's acids
Mahoney, Stuart J.,Moon, David T.,Hollinger, Jon,Fillion, Eric
, p. 4706 - 4709 (2011/03/18)
Under Sc(OTf)3 catalysis, benzylidene Meldrum's acids bearing a tethered p-methoxyphenethyl group were observed to undergo a [1,5]-hydride shift/cyclization at room temperature, representing a mild Csp3-H bond functionalization. The resulting spiro Meldrum's acid intermediates then underwent intramolecular Friedel-Crafts acylation, completing the one-pot, domino reaction. The reported protocol generates the 6-6-5-6 tetracyclic core of tetrahydrobenzo[b]fluoren-11-ones.
Oxaziridine-mediated intramolecular amination of sp3-hybridized c-h bonds
Allen, Charles P.,Benkovics, Tamas,Turek, Amanda K.,Yoon, Tehshik P.
supporting information; experimental part, p. 12560 - 12561 (2010/01/29)
(Chemical Equation Presented) We describe a new oxaziridine-mediated approach to the amination of sp3-hybridized C-H bonds. In the presence of a copper(II) catalyst, N-sulfonyl oxaziridines participate in efficient intramolecular cyclization re
