- Electrophilic Cyanation of Boron Enolates: Efficient Access to Various β-Ketonitrile Derivatives
-
The highly efficient electrophilic cyanation of boron enolates using readily available cyanating reagents, N-cyano-N-phenyl-p-toluenesulfonamide (NCTS) and p-toluenesulfonyl cyanide (TsCN), is reported. Various β-ketonitriles were prepared by this new protocol, which has a remarkably broad substrate scope compared to existing methods. The present method also allowed efficient synthesis of β-ketonitriles containing a quaternary α-carbon center. In addition, a preliminary result with the use of a chiral boron enolate for the enantioselective cyanation reaction is described.
- Kiyokawa, Kensuke,Nagata, Takaya,Minakata, Satoshi
-
supporting information
p. 10458 - 10462
(2016/08/24)
-
- An Alternative to the Classical α-Arylation: The Transfer of an Intact 2-Iodoaryl from ArI(O2CCF3)2
-
The α-arylation of carbonyl compounds is generally accomplished under basic conditions, both under metal catalysis and via aryl transfer from the diaryl λ3-iodanes. Here, we describe an alternative metal-free α-arylation using ArI(O2CCF3)2 as the source of a 2-iodoaryl group. The reaction is applicable to activated ketones, such as α-cyanoketones, and works with substituted aryliodanes. This formal C-H functionalization reaction is thought to proceed through a [3,3] rearrangement of an iodonium enolate. The final α-(2-iodoaryl)ketones are versatile synthetic building blocks.
- Jia, Zhiyu,Gálvez, Erik,Sebastián, Rosa María,Pleixats, Roser,álvarez-Larena, ángel,Martin, Eddy,Vallribera, Adelina,Shafir, Alexandr
-
supporting information
p. 11298 - 11301
(2016/02/19)
-
- FURO[3,2-D]PYRIMIDINE DERIVATIVES
-
Furo[3,2-d]pyrimidine derivatives of formula I, wherein the meanings for the various substituents are as defined in the description. These compounds are useful as H4 receptor antagonists.
- -
-
Page/Page column 58-59
(2009/06/27)
-
- A modified Robinson annulation process to α,α-disubstituted-β,γ-unsaturated cyclohexanone system. Application to the total synthesis of nanaimoal
-
4-Cyano-2-cyclohexenones were found to be susceptible to reductive alkylation reactions, giving the corresponding 2,2-disubstituted-3-cyclohexenone derivatives in a completely regioselective manner. This newly developed methodology has been successfully applied towards the total synthesis, in racemic form, of the marine natural product nanaimoal.
- Liu, Hsing-Jang,Ly, Tai Wei,Tai, Chia-Liang,Wu, Jen-Dar,Liang, Jinn-Kwei,Guo, Jiunn-Cheh,Tseng, Nai-Wen,Shia, Kak-Shan
-
p. 1209 - 1226
(2007/10/03)
-