1140969-67-0Relevant academic research and scientific papers
Dinuclear Zinc-AzePhenol Catalyzed Asymmetric Aza-Henry Reaction of N-Boc Imines and Nitroalkanes under Ambient Conditions
Liu, Shanshan,Gao, Wen-Chao,Miao, Yu-Hang,Wang, Min-Can
, p. 2652 - 2659 (2019/02/26)
The asymmetric aza-Henry reaction of N-Boc imines and nitroalkanes was realized in the presence of 10 mol % dinuclear zinc-AzePhenol catalysts under ambient conditions. A variety of nitroamines were obtained in good yields (up to 97%) with excellent enantioselectivities (up to 99% ee) and high diasteroselectivity (up to 14:1 dr). Our protocol combined the operational simplicity and mild reaction conditions, thus making the process amenable for technical applications.
Enantioselective aza-Henry reaction of: t -Boc protected imines and nitroalkanes with bifunctional squaramide organocatalysts
Susam, Dil?ad,Tanyeli, Cihangir
, p. 3555 - 3561 (2017/07/12)
An organocatalytic asymmetric aza-Henry reaction of t-Boc protected imines with nitroalkanes has been established by chiral acid-base type bifunctional Cinchona alkaloid/squaramide organocatalysts. The cooperation of a quinine motif as a base and sterical
Modular bifunctional chiral thioureas as versatile organocatalysts for highly enantioselective aza-Henry reaction and michael addition
Li, Hua,Zhang, Xu,Shi, Xin,Ji, Nan,He, Wei,Zhang, Shengyong,Zhang, Bangle
, p. 2264 - 2274 (2012/11/06)
A series of new modular bifunctional chiral thiourea organocatalysts were synthesized from natural Cinchona alkaloids and amino acids, and their performance in the aza-Henry reaction of nitroalkanes to imines, the Michael addition of acetylacetone to nitroolefins and the Michael addition of acetone to nitroolefins was investigated. Under the mild conditions, the important building blocks β-nitro amines and γ-nitro carbonyl compounds could be obtained in good yields (up to 95%) with excellent enantioselectivities (up to 99% ee) and diastereoselectivity (up to 17:1). Copyright
Doubly stereocontrolled asymmetric aza-henry reaction with in situ generation of n-boc-imines catalyzed by novel rosin-derived amine thiourea catalysts
Jiang, Xianxing,Zhang, Yifu,Wu, Lipeng,Zhang, Gen,Liu, Xing,Zhang, Hailong,Fu, Dan,Wang, Rui
supporting information; experimental part, p. 2096 - 2100 (2009/12/27)
The doubly stereocontrolled organocatalytic aza-Henry reaction of nitroalkanes to N-Bocimines generated in situ from a variety of substituted α-amido sulfones was investigated for the first time, in general, affording the corresponding products with high
Reversal of enantioselectivity using tethered bisguanidine catalysts in the aza-Henry reaction
Lovick, Helena M.,Michael, Forrest E.
scheme or table, p. 1016 - 1019 (2009/05/27)
A series of chiral guanidines were synthesized and shown to efficiently catalyze the aza-Henry reaction. Modifications of the catalyst structure revealed important selectivity trends as well as an intriguing reversal in stereoselectivity with bisguanidine
A novel bis-thiourea organocatalyst for the asymmetric aza-Henry reaction
Rampalakos, Constantinos,Wulff, William D.
supporting information; experimental part, p. 1785 - 1790 (2009/08/07)
A novel bis-thiourea/2,2′-diaminobinaphthalene (BINAM)-based catalyst for the asymmetric aza-Henry reaction has been developed. This catalyst promotes the reaction of N-Boc imines with nitroalkanes to afford β-nitroamines with good yields and high enantioselectivities. This catalyst has the advantage that it can be prepared in a single step from commercially available materials. A model is proposed for the catalyst action where both components of the reaction are activated simultaneously by hydrogen bonding. Regardless of the mechanism, the success of the present catalyst demonstrates the potential of bis-thioureas as an interesting class of relatively unexplored catalysts.
