63160-16-7Relevant academic research and scientific papers
Asymmetric Friedel-Crafts addition of indoles to N-sulfonyl aldimines: A simple approach to optically active 3-indolyl-methanamine derivatives
Jia, Yi-Xia,Xie, Jian-Hua,Duan, Hai-Feng,Wang, Li-Xin,Zhou, Qi-Lin
, p. 1621 - 1624 (2006)
The enantioselective copper(II)-catalyzed Friedel-Crafts addition of indoles to N-sulfonyl aldimines was developed using chiral bisoxazoline as ligands, and high enantioselectivities (up to 96% ee) were achieved.
TfOH-catalyzed formal [3+2] cycloaddition of N-tosylaziridine dicarboxylates and nitriles: Synthesis of tetrafunctionalized 2-imidazolines
Zuo, Qinglu,Shi, Zhichao,Zhan, Feng,Wang, Zhe,Lin, Jin-Shun,Jiang, Yuyang
supporting information, (2020/01/13)
We developed an efficient method for synthesis of tetrafunctionalized 2-imidazolines using TfOH-catalyzed formal [3+2] cycloaddition of N-tosylaziridine dicarboxylates and nitriles. This is the first report of C–N bond cleavage of N-tosylaziridine dicarboxylates catalyzed by Br?nsted acid and the reaction worked well over wide scope of substrates in good to excellent yields under mild conditions. The method has the potential to be applied to pharmaceutical design and synthesis of tetrafunctionalized 2-imidazolines.
The Generation of Difluoroketenimine and Its Application in the Synthesis of α,α-Difluoro-β-amino Amides
Zhang, Rui,Zhang, Zhikun,Zhou, Qi,Yu, Lefei,Wang, Jianbo
supporting information, p. 5744 - 5748 (2019/03/28)
Fluorine-containing β-amino acids and their derivatives have attracted significant attention due to their importance in life sciences. Herein the previously unknown difluoroketenimine, the analogue of the elusive difluoroketene, has been generated by the
Synthesis of Benzyl Amines via Copper-Catalyzed Enantioselective Aza-Friedel-Crafts Addition of Phenols to N -Sulfonyl Aldimines
Shikora, Jonathan M.,Chemler, Sherry R.
supporting information, p. 2133 - 2137 (2018/04/30)
A new copper-catalyzed enantioselective aza-Freidel-Crafts reaction between phenols and N-sulfonyl aldimines that provides chiral secondary benzylamines in good to excellent yields and excellent enantioselectivities (up to 99% ee) is disclosed. In particular, excellent scope with alkylimines was observed for the first time. The synthetic utility of the products was demonstrated in the first enantioselective synthesis of a dual orexin receptor antagonist, a compound that contains an amine-bearing stereocenter adjacent to a bis-ortho-functionalized arene.
Formation of: N -sulfonyl imines from iminoiodinanes by iodine-promoted, N-centered radical sulfonamidation of aldehydes
Hopkins, Megan D.,Scott, Kristina A.,Demier, Brettany C.,Morgan, Heather R.,Macgruder, Jesse A.,Lamar, Angus A.
, p. 9209 - 9216 (2017/11/14)
A mild and operationally convenient formation of synthetically valuable N-sulfonyl imines from a range of aryl aldehydes by reaction with iminoiodinanes (PhINZ) and I2 has been developed. According to mechanistic experiments described within, the reaction is speculated to proceed through an unconventional light-promoted, N-centered radical (NCR) pathway involving a N,N-diiodosulfonamide reactive species. This method not only provides a new pathway toward the production of activated imines, but also serves as an example of a non-traditional means of carbonyl activation via an NCR species.
Probing the Diastereoselectivity of Staudinger Reactions Catalyzed by N-Heterocyclic Carbenes
Hans, Morgan,Wouters, Johan,Demonceau, Albert,Delaude, Lionel
supporting information, p. 10870 - 10877 (2015/07/20)
The reaction of ethylphenylketene with 1,3-dimesitylimidazol-2-ylidene (IMes) or 1,3-dimesitylimidazolin-2-ylidene (SIMes) afforded the corresponding azolium enolates in high yields. The two zwitterions were fully characterized by various analytical techn
Catalytic asymmetric synthesis of dihydroquinazolinones from imines and 2-aminobenzamides
Cheng, Dao-Juan,Tian, Yu,Tian, Shi-Kai
supporting information; experimental part, p. 995 - 999 (2012/06/01)
An unprecedented catalytic asymmetric synthesis of aminal-containing heterocyclic compounds has been developed from imines and tethered nitrogen/nitrogen nucleophiles. In the presence of 10mol% of a commercially available chiral phosphoric acid, a range of aromatic, α,β- unsaturated, and aliphatic imines react with 2-aminobenzamides to give dihydroquinazolinones in good to excellent yields and ee. The enantioselectivity is significantly affected by the imine N-substituent through non-bonding interactions with the chiral phosphoric acid and the 2-aminobenzamide. Copyright
Rhodium-catalyzed synthesis of branched amines by direct addition of benzamides to imines
Hesp, Kevin D.,Bergman, Robert G.,Ellman, Jonathan A.
supporting information; experimental part, p. 2304 - 2307 (2012/06/30)
Rhodium-catalyzed addition of benzamide C-H bonds to a range of aromatic N-sulfonyl aldimines has been developed and proceeds with high functional group compatibility. The synthetic utility of the resulting branched amine products has also been demonstrated by the preparation of isoindoline and isoindolinone frameworks.
Rhodium(III)-catalyzed arylation of Boc-imines via C-H bond functionalization
Tsai, Andy S.,Tauchert, Michael E.,Bergman, Robert G.,Ellman, Jonathan A.
supporting information; experimental part, p. 1248 - 1250 (2011/04/16)
The first rhodium-catalyzed arylation of imines proceeding via C-H bond functionalization is reported. Use of a non-coordinating halide abstractor is important to obtain reactivity. Aryl-branched N-Boc-amines are formed, and a wide range of functionality is compatible with the reaction.
One-pot nitro-Mannich/hydroamination cascades for the direct synthesis of 2,5-disubstituted pyrroles using base and gold catalysis
Barber, David M.,Sanganee, Hitesh,Dixon, Darren J.
supporting information; body text, p. 4379 - 4381 (2011/06/17)
An efficient, easy to perform, one-pot reaction cascade for the synthesis of 2,5-disubstituted pyrroles from p-toluenesulfonyl protected imines and 4-nitrobut-1-yne under a combination of base and gold(iii) catalysis is reported.
