4835-96-5Relevant articles and documents
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Farmer,R.F.,Hamer,J.
, p. 2418 - 2419 (1966)
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Marvel,Frank
, p. 1675,1677 (1942)
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Stereoselective synthesis of novel C-3 functionalized 3-sulfonyl-β-lactams: Promising biologically active heterocyclic scaffolds
Bhalla, Aman,Modi, Garima,Bari, Shamsher S.,Kumari, Anu,Berry, Shiwani,Hundal, Geeta
, p. 1160 - 1165 (2017)
An efficient and operationally simple strategy for the stereoselective synthesis of novel C-3 functionalized 3-sulfonyl-β-lactam heterocycles is described. The C-3 functionalized 3-phenyl/benzylsulfonyl-β-lactams 3/3′, 5/5′ has been synthesized via Michael addition using different Michael acceptors on trans-3-phenyl/benzylsulfonyl-β-lactams 2(a–f) using K2CO3as a base and acetonitrile/DMF as solvents. The reaction furnished exclusively cis-β-lactam adducts 3(a–r) using sterically less hindered Michael acceptors. Further, the effect of steric bulk and chiralilty of Michael acceptors was explored to achieve target C-3 functionalized β-lactams 3(s-u)/3′(s-u) and 5(a–c)/5′(a–c). The structural and stereochemical analysis of novel β-lactams were carried out using FT-IR, NMR (1H,13C,1H-1H COSY,1H-13C COSY and13C DEPT-135), elemental analysis (CHNS), mass spectrometry (EIMS and LCMS) in representative cases and single crystal X-ray crystallographic studies (3e). The cis or trans configuration of the Michael acceptor (E) at C-3 was assigned with respect to C4-H.
Trifluoromethyl allyl compound as well as preparation method and application thereof
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Paragraph 0036-0040, (2021/08/06)
The invention discloses a trifluoromethyl allyl compound as well as a preparation method and application thereof. According to the method, allyl alcohol is directly used as a raw material, CF3SO2Na is selected as a trifluoromethylation reagent, a metal-free and cheap photooxidation reduction catalyst is used, and under the catalysis of an organic photooxidation reduction agent, a byproduct SO2 generated in situ is reused as an activated C-OH bond, so that the reaction is carried out in an environment-friendly manner under a mild condition. The allyl alcohol used in the preparation method disclosed by the invention is a MoritA-Baylis-Hillman alcohol allyl alcohol raw material which is simple to synthesize and high in conversion rate, the applicable substrate range is wide, and the preparation cost is low. In addition, the preparation method disclosed by the invention is simple in steps, and has the characteristics of convenience in operation, environment friendliness, excellent stereoselectivity and broad-spectrum functional group tolerance. The trifluoromethyl allyl compound provided by the invention is a general precursor for preparing related CF3 molecules, has potential pharmaceutical activity and biological activity, and can be widely applied to biological and pharmaceutical active molecules.
Acid- And base-switched palladium-catalyzed γ-C(sp3)-H alkylation and alkenylation of neopentylamine
Zhang, Jinquan,Zhang, Shuaizhong,Zou, Hongbin
supporting information, p. 3466 - 3471 (2021/05/31)
The functionalization of remote unactivated C(sp3)-H and the reaction selectivity are among the core pursuits for transition-metal catalytic system development. Herein, we report Pd-catalyzed γ-C(sp3)-H-selective alkylation and alkenylation with removable 7-azaindole as a directing group. Acid and base were found to be the decisive regulators for the selective alkylation and alkenylation, respectively, on the same single substrate under otherwise the same reaction conditions. Various acrylates were compatible for the formation of C(sp3)-C(sp3) and C(sp3)-C(sp2) bonds. The alkenylation protocol could be further extended to acrylates with natural product units and α,β-unsaturated ketones. The preliminary synthetic manipulation of the alkylation and alkenylation products demonstrates the potential of this strategy for structurally diverse aliphatic chain extension and functionalization. Mechanistic experimental studies showed that the acidic and basic catalytic transformations shared the same six-membered dimer palladacycle.