188626-56-4Relevant academic research and scientific papers
Two Distinct Ag(I)- And Au(I)-Catalyzed Olefinations between α-Diazo Esters and N-Boc-Derived Imines
Kardile, Rahul Dadabhau,Liu, Rai-Shung
, p. 6452 - 6456 (2019/09/06)
Metal-catalyzed reactions between α-diazo esters and imines were well-known to yield aziridine derivatives exclusively. This work reports two new olefination reactions between N-Boc-derived (Boc = tert-Butyloxycarbonyl) imines and α-diazo esters with Ag(I) and Au(I) catalysts, respectively. Our mechanistic studies reveal that these new olefinations involve an initial attack of diazo esters on metal/imine complexes to form Mannich-addition intermediates, which subsequently afford α-aryl-β-aminoacrylates via a Roskamp reaction, or to form β-aryl-β-aminoacrylates via the formation of silver carbenes.
Interception of Radicals by Molecular Oxygen and Diazo Compounds: Direct Synthesis of Oxalate Esters Using Visible-Light Catalysis
Ma, Meihua,Hao, Weiwei,Ma, Liang,Zheng, Yonggao,Lian, Pengcheng,Wan, Xiaobing
, p. 5799 - 5802 (2018/09/12)
The synthesis of oxalate esters through a radical process, rather than the traditional ionic reaction, has been well developed in which the radicals induced by visible light are trapped by molecular oxygen and diazo compounds under room temperature. This reaction is operationally simple, mild, and shows broad substrate scopes in α-bromo ketones and diazo compounds.
In Situ Generation of Quinolinium Ylides from Diazo Compounds: Copper-Catalyzed Synthesis of Indolizine
Chen, Rongxiang,Zhao, Yanwei,Sun, Hongmei,Shao, Ying,Xu, Yudong,Ma, Meihua,Ma, Liang,Wan, Xiaobing
, p. 9291 - 9304 (2017/09/22)
The Cu-catalyzed three-component reaction between quinolines, diazo compounds, and alkenes has been established for direct construction of indolizine derivatives via quinolinium ylides. This methodology is distinguished by the use of a commercially inexpensive catalyst and readily available starting materials, wide substrate scope, and operational simplicity.
Intramolecular cyclopropanation of bromodiazoacetates
Bolsones, Marianne,Bonge-Hansen, Hanne Therese,Bonge-Hansen, Tore
, p. 221 - 224 (2014/02/14)
A series of allylic diazoacetates were prepared from the corresponding allylic alcohols and bromoacetyl bromide. When the allylic diazoacetates were treated with 1,8-diazabicyclo[5.4.0]undec-7-ene and N-bromosuccinimide, a rapid full conversion to the corresponding allylic bromodiazoacetates occurred. Exposure of the allylic bromodiazoacetates to rhodium(II) catalysts induced an intramolecular cyclopropanation and gave cyclopropyl bromolactones in yields that were low to good, depending on the substitution pattern. Georg Thieme Verlag Stuttgart New York.
Highly asymmetric intramolecular cyclopropanation of acceptor-substituted diazoacetates by Co(II)-based metalloradical catalysis: Iterative approach for development of new-generation catalysts
Xu, Xue,Lu, Hongjian,Ruppel, Joshua V.,Cui, Xin,Lopez De Mesa, Silke,Wojtas, Lukasz,Zhang, X. Peter
, p. 15292 - 15295 (2011/11/04)
3,5-DitBu-QingPhyrin, a new D2-symmetric chiral porphyrin derived from a chiral cyclopropanecarboxamide containing two contiguous stereocenters, has been developed using an iterative approach based on Co(II)-catalyzed asymmetric cyclopropanation of alkenes. The Co(II) complex of 3,5-DitBu-QingPhyrin, [Co(P2)], has proved to be a general and effective catalyst for asymmetric intramolecular cyclopropanation of various allylic diazoacetates (especially including those with α-acceptor substituents) in high yields with excellent stereoselectivities. The [Co(P2)]-based intramolecular metalloradical cyclopropanation provides convenient access to densely functionalized 3-oxabicyclo[3.1.0]hexan-2-one derivatives bearing three contiguous quaternary and tertiary chiral centers with high enantiomeric purity.
