1174514-08-9Relevant academic research and scientific papers
Bifunctional Phase-Transfer Catalysts Catalyzed Diastereo- and Enantioselective Aza-Henry Reaction of β,γ-Unsaturated Nitroalkenes With Amidosulfones
Lu, Ning,Bai, Fuquan,Fang, Yanhong,Wei, Zhonglin,Cao, Jungang,Liang, Dapeng,Lin, Yingjie,Duan, Haifeng
, p. 4111 - 4116 (2017)
An efficient diastereo- and enantioselective aza-Henry reaction of β,γ-unsaturated nitroalkenes with N-Boc amidosulfones has been realized under the catalysis of bifunctional chiral phase-transfer catalysts bearing multiple H-bonding donors, which was derived from cinchona alkaloids. This asymmetric catalytic protocol is suitable for a wide range of substrates, and give the corresponding products in high to excellent yields (up to 99%) with excellent diastereo- and enantioselectivities (up to >99 : 1 dr, up to >99% ee). Density functional theory (DFT) calculations are also performed and give the possible transition-state model to illustrate the mechanism of the developed reaction. (Figure presented.).
Nitroolefins as a nucleophilic component for highly stereoselective aza Henry reaction under the catalysis of chiral ammonium betaines
Uraguchi, Daisuke,Oyaizu, Keigo,Ooi, Takashi
, p. 8306 - 8309 (2012)
Vinylogous nitronate was successfully generated from β,β- disubstituted nitroolefins for achieving a highly regio-, diastereo-, and enantioselective aza Henry reaction under the influence of chiral ammonium betaine of type 1 as an organic-base catalyst. The present approach greatly expands the synthetic utility of nitroolefins in the development of carbon-carbon bond-forming reactions (see scheme). Copyright
Diastereo- and enantioselective Aza-MBH-type reaction of nitroalkenes to N-tosylimines catalyzed by bifunctional organocatalysts
Wang, Xiao,Chen, Yong-Fei,Niu, Liang-Feng,Xu, Peng-Fei
scheme or table, p. 3310 - 3313 (2009/12/05)
The first example of diastereo- and enantioselective aza-MBH-type reaction was accomplished by the asymmetric synthesis of β-nitro-γenamines via a (1R,2R)-diaminocyclohexane thiourea derivative mediated tandem Michael addition and aza-Henry reaction in good yields (up to 95%) and high enantioselectivities (up to 91% ee) and diastereoselectivities (up to 1:99 dr).
