879563-65-2Relevant academic research and scientific papers
Photochemical benzylic bromination in continuous flow using BrCCl3 and its application to telescoped p-methoxybenzyl protection
Otake, Yuma,Williams, Jason D.,Rincón, Juan A.,De Frutos, Oscar,Mateos, Carlos,Kappe, C. Oliver
, p. 1384 - 1388 (2019)
BrCCl3 represents a rarely used benzylic brominating reagent with complementary reactivity to other reagents. Its reactivity has been revisited in continuous flow, revealing compatibility with electron-rich aromatic substrates. This has brought about the development of a p-methoxybenzyl bromide generator for PMB protection, which was successfully demonstrated on a pharmaceutically relevant intermediate on 11 g scale, giving 91% yield and a PMB-Br space-time-yield of 1.27 kg L?1 h?1
Stereoselective Total Synthesis of KAE609 via Direct Catalytic Asymmetric Alkynylation to Ketimine
Takada, Hisashi,Kumagai, Naoya,Shibasaki, Masakatsu
supporting information, p. 4762 - 4765 (2015/10/12)
A direct catalytic asymmetric alkynylation protocol is applied to provide the requisite enantioenriched propargylic α-tertiary amine, allowing for the stereoselective total synthesis of KAE609 (formerly NITD609 or cipargamin).
Synthesis and antiproliferative evaluation of hybrids of indolin-2-one and quinazoline-4(3H)-one linked via imine bond
Wu, Wei-Yao,Cao, Sheng-Li,Mao, Bei-Bei,Liao, Ji,Li, Zhong-Feng,Song, Hao-Bin,Xu, Xingzhi
, p. 61 - 66 (2013/08/22)
A novel series of hybrids of indolin-2-one and quinazolin-4(3H)-one linked via an imine bond were synthesized and tested for their inhibitory activity against the proliferation of a panel of five human cancer cell lines. We found that compound 5c bearing
Me-BIPAM for the synthesis of optically active 3-aryl-3-hydroxy-2-oxindoles by ruthenium-catalyzed addition of arylboronic acids to isatins
Yamamoto, Yasunori,Miyaura, Norio,Yohda, Masaaki,Shirai, Tomohiko,Ito, Hajime
supporting information, p. 2446 - 2449,4 (2020/08/24)
A chiral O-linked C2-symmetric bidentate phosphoramidite (Me-BIPAM) was found to be efficient for the ruthenium-catalyzed addition of arylboronic acids to isatins. Asymmetric synthesis of 3-aryl-3-hydroxy-2- oxindoles by 1,2-addition of arylboronic acids to isatins was carried out in the presence of [RuCl2(PPh3)3]/(R,R)-Me-BIPAM and KF, resulting in an enantioselectivity as high as 90 % ee. It was found that the reaction with N-protected isatins proceeds with high yields and good enantioselectivities. The best protective groups on the nitrogen atom were different depending on the substituents on the aromatic ring. The use of a N-benzyl group resulted in excellent enantioselectivities in many substrates compared with other groups. Add it up: A chiral O-linked C2-symmetric bidentate phosphoramidite (Me-BIPAM) was found to be efficient for the ruthenium-catalyzed addition of arylboronic acids to isatins. Asymmetric synthesis of 3-aryl-3-hydroxy-2-oxindoles by 1,2-addition of arylboronic acids to isatins was carried out in the presence of [RuCl2(PPh 3)3]/(R,R)-Me-BIPAM and KF, resulting in an enantioselectivity as high as 90 % ee. Copyright
Rhodium-catalyzed asymmetric addition of aryl- and alkenylboronic acids to isatins
Shintani, Ryo,Inoue, Mitsunori,Hayashi, Tamio
, p. 3353 - 3356 (2008/02/11)
(Chemical Equation Presented) Mopping up the rhodium: A rhodium-catalyzed asymmetric addition of aryl-boronic acids to isatins has been developed to produce biologically relevant 3-aryl-3-hydroxy-2-oxindoles in high yield (see scheme). High enantioselectivity was observed with (R)-MeO-mop as a ligand, and the reaction could be extended to the addition of alkenyl groups.
