95729-83-2Relevant academic research and scientific papers
The development of new amine-amide ligands for application in Cu(II)-catalyzed enantioselective Henry reactions
Ao, Chunyan,Men, Jian,Wang, Yang,Shao, Tao,Huang, Yuanyuan,Huo, Junji,Gao, Guowei
, p. 589 - 595 (2016/07/06)
A new type of chiral tertiary amine ligand was designed and derived from l-proline and (R)-BINOL. These new chiral ligands chelated with Cu(II) showed highly catalytic efficiency in enantioselective Henry reactions. Excellent yields (up to 99%) and high enantioselectivities (up to 96% ee) were achieved for aromatic, hetero-aromatic and aliphatic aldehyde substrates, without an additional base additive or the need for air or moisture exclusion.
Chiral amine catalyzed enantio- and diastereoselective Michael reaction in brine
Singh, Sarbjit,Chimni, Swapandeep Singh
, p. 1068 - 1079 (2012/11/06)
Simple pyrrolidine-based chiral amines were synthesized and used for the Michael addition of different ketones to a variety of nitro-olefins in brine. The effect of different surfactants and acids on the yields and stereochemical outcome of the Michael ad
Simple and facile l-prolinamides derived from achiral cycloalkylamines as organocatalysts for the highly efficient large-scale asymmetric direct aldol reactions
Xu, Jiang-Wei,Fu, Xiang-Kai,Hu, Xiao-Yan,Wu, Chuan-Long
experimental part, p. 1156 - 1163 (2012/06/18)
A series of N-cycloalkylprolinamides have been designed and synthesized from achiral cycloalkylamines in a facile manner. They promoted high stereoselectivity in the cross-aldol reaction. N-cyclopropylprolinamide performed best with a smallest carbocyclic
Asymmetric intramolecular aldol reaction mediated by (S)-N-substituted-N- (2-pyrrolidinylmethyl)amine to prepare Wieland-Miescher ketone
Akahane, Yuichi,Inomata, Kohei,Endo, Yasuyuki
experimental part, p. 1727 - 1737 (2011/06/17)
New or known N-substituted-N-(2-pyrrolidinylmethyl)amine derivatives bearing a variety of alkyl and aryl substituents were easily prepared from N-Boc-proline or N-Boc-N-(2-pyrrolidinylmethyl)amine. The enantioselectivity of the intramolecular asymmetric aldol reaction mediated by a combination of the amine derivative and TFA to prepare Wieland-Miescher ketone was examined. During the examination, optimal amount of TFA in the reaction was identified. The Japan Institute of Heterocyclic Chemistry.
Simple, inexpensive, and facile l-prolinamide used as a recyclable organocatalyst for highly efficient large-scale asymmetric direct aldol reactions
Xu, Jiangwei,Fu, Xiangkai,Wu, Chuanlong,Hu, Xiaoyan
experimental part, p. 840 - 850 (2011/08/21)
In order to discover a simple, inexpensive, and efficient route to obtain highly enantiomerically enriched anti-aldol products for applications in industry, a series of prolinamides 1-5 with different carbocyclic rings have been synthesized from achiral c
An N,N′-dioxide/In(OTf)3 catalyst for the asymmetric hetero-Diels-Alder reaction between Danishefsky's dienes and aldehydes: Application in the total synthesis of triketide
Yu, Zhipeng,Liu, Xiaohua,Dong, Zhenhua,Xie, Mingsheng,Feng, Xiaoming
, p. 1308 - 1311 (2008/12/22)
(Chemical Equation Presented) In-teresting catalyst: An asymmetric hetero Diels-Alder reaction between Danishefsky's dienes and various aldehydes using an N,N′-dioxide/In(OTf)3 complex affords highly substituted chiral dihydropyranones with up
Enantioselective Strecker reaction of phosphinoyl ketoimines catalyzed by in situ prepared chiral N,N′-dioxides
Huang, Jinglun,Liu, Xiaohua,Wen, Yuehong,Qin, Bo,Feng, Xiaoming
, p. 204 - 208 (2007/10/03)
The enantioselective Strecker reaction of N-diphenylphosphinoyl ketoimines has been achieved by use of in situ prepared chiral N,N′-dioxide catalyst from L-piperidinamide 3f and m-chloroperoxybenzoic acid (m-CPBA). Excellent yields (up to 99%) and high enantioselectivities (up to 92% ee) were obtained. In particular, in situ prepared catalyst with readily available chiral material made the procedure more convenient. Moreover, the L-piperidinamide 3f-derived N,N′-dioxide 9 could be recycled and reused at least five times without any loss of either catalytic activity or enantioselectivity.
Enantioselective cyanosilylation of α,α-dialkoxy ketones catalyzed by proline-derived in-situ-prepared N-oxide as bifunctional organocatalyst
Qin, Bo,Liu, Xiaohua,Shi, Jian,Zheng, Ke,Zhao, Haitao,Feng, Xiaoming
, p. 2374 - 2378 (2007/10/03)
Bifunctional N,N′-dioxide catalysts have been developed for highly enantioselective cyanosilylation of α,α-dialkoxy ketones. This process, catalyzed by in-situ-prepared proline-derived N,N′-dioxide 2b, produced the corresponding cyanohydrin trimethylsilyl ethers in excellent yields (up to 99%) with high enantioselectivities (up to 93% ee). A reasonable mechanism was proposed according to the observation of the linear effect, 1H NMR spectra, isolated cyanohydrin, and the roles of the NH and N-oxide moieties of the catalyst.
Chiral bisformamides as effective organocatalysts for the asymmetric one-pot, three-component strecker reaction
Wen, Yuehong,Xiong, Yan,Chang, Lu,Huang, Jinglun,Liu, Xiaohua,Feng, Xiaoming
, p. 7715 - 7719 (2008/02/12)
(Chemical Equation Presented) C2-symmetric chiral bisformamides have been shown to catalyze the asymmetric one-pot, three-component Strecker reaction, which produced the α-amino nitriles in excellent yields (up to 99%) with good enantioselectiv
Asymmetric cyanosilylation of aldehydes catalyzed by novel organocatalysts
Wen, Yuehong,Huang, Xiao,Huang, Jinglun,Xiong, Yan,Qin, Bo,Feng, Xiaoming
, p. 2445 - 2448 (2007/10/03)
A novel proline-based N,N′-dioxide, which is easily prepared from inexpensive chemicals, serves as an effective catalyst for enantioselective cyanosilylation of aldehydes in up to 73% ee. Georg Thieme Verlag Stuttgart.
