Investigation of the palladium-catalysed cyclisation of α-amido malonates with propargylic compounds

Barlow, Sean R.; L, Callaghan; Franckevičius, Vilius

doi:10.1016/j.tet.2020.131866

Cited by 3 publications

(4 citation statements)

References 86 publications

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“…13 C NMR (101 MHz) δ 173.2 (C=O), 171.5 (C=O), 161.6 (C=N), 152.1 (CHAr), 150.6 (CHAr), 134.9 (CHAr), 131.1 (CAr), 123.6 (CHAr), 71.7 (CH), 52.3 (CH 3 ), 51.7 (CH 3 ), 30.1 (CH 2 ), 28.2 (CH 2 ). MS (EI) m/z: 264 (M + , 7%), 205 (74), 204 (43), 191 (26), 145 (100), 118 (27), 105 (38). HRMS (ESI): m/z calcd for C 13 H 16 N 2 O 4 [M + ] 264.111; found: 264.1108.…”

Section: General Experimental Procedures For the Synthesis Of Michael...mentioning

confidence: 99%

“…HRMS (ESI): m/z calcd for C 16 (35), 112 (44), 110 (29), 96 (44), 57 (51), 43 (36), 41 (23) (20), 236 (20), 184 (20), 160 (48), 89 (35), 57 (31), 43 (24) 13 C NMR (101 MHz) δ 172.1 (C=O), 171.9 (C=O), 162.9 (CH=N), 134.5 (CAr), 131.8 (CHAr), 129.9 (CHAr), 125.6 (BrCAr), 71.6 (NCHCO 2 Me), 52.2 (CO 2 CH 3 ), 37.1 (NCH 3 ), 35.9 (NCH 3 ), 28.9 (CH 2 ), 28.7 (CH 2 ). MS (EI) m/z: 354 (M + , 5%), 270 (30), 268 (32), 224 (35), 222 (31), 173 (24), 100 (26), 89 (31), 87 (100), 72 (35), 45 (25) 13 C NMR (101 MHz) δ 172.1 (C=O), 171.9 (C=O), 162.9 (CH=N), 134.5 (CAr), 131.8 (CHAr), 129.9 (CHAr), 125.7 (BrCAr), 71.6 (NCHCO 2 Me), 52.2 (CO 2 CH 3 ), 37.1 (NCH 3 ), 35.3 (NCH 3 ), 28.9 (CH 2 ), 28.7 (CH 2 ). MS (EI) m/z: 354 (M + , 5%), 270 (30), 268 (32), 224 (35), 222 (31), 173 (24), 100 (26), 89 (31), 87 (100), 72 (35), 45 (25).…”

Section: -(Tert-butyl) 1-methyl (E)-2-[(pyridin-3-ylmethylenementioning

confidence: 99%

“…MS (EI) m/z: 354 (M + , 5%), 270 (30), 268 (32), 224 (35), 222 (31), 173 (24), 100 (26), 89 (31), 87 (100), 72 (35), 45 (25) 13 C NMR (101 MHz) δ 172.1 (C=O), 171.9 (C=O), 162.9 (CH=N), 134.5 (CAr), 131.8 (CHAr), 129.9 (CHAr), 125.7 (BrCAr), 71.6 (NCHCO 2 Me), 52.2 (CO 2 CH 3 ), 37.1 (NCH 3 ), 35.3 (NCH 3 ), 28.9 (CH 2 ), 28.7 (CH 2 ). MS (EI) m/z: 354 (M + , 5%), 270 (30), 268 (32), 224 (35), 222 (31), 173 (24), 100 (26), 89 (31), 87 (100), 72 (35), 45 (25). HRMS (ESI): m/z calc for C 15 H 19 BrN 2 O 3 [M + ] 354.0579; found: 354.0565.…”

Section: -(Tert-butyl) 1-methyl (E)-2-[(pyridin-3-ylmethylenementioning

confidence: 99%

“…Considering this last approach, α-substituted glutamates have been mainly obtained via the Michael-type additions of glycine derivatives (glycine templates) onto the corresponding α,β-unsaturated reagents. This reliable strategy employs N -arylidene-α-amino acid esters [ 14 , 15 , 16 ] or tert -butyl N -benzylidieneamino glycinate [ 17 , 18 , 19 , 20 , 21 , 22 ] ( Scheme 1 a) and even activated N -arylideneaminomalonates [ 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 ] ( Scheme 1 b) as starting materials. In all cases, phase transfer catalysis (PTC) conditions or the employment of organic superbases are the most common trends to complete the reaction.…”

Section: Introductionmentioning

confidence: 99%

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Phosphine Catalyzed Michael-Type Additions: The Synthesis of Glutamic Acid Derivatives from Arylidene-α-amino Esters

Rodríguez-Flórez,

González-Marcos,

García-Mingüens

et al. 2024

Molecules

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The reaction of arylidene-α-amino esters with electrophilic alkenes to yield Michael-type addition compounds is optimized using several phosphines as organocatalysts. The transformation is very complicated due to the generation of several final compounds, including those derived from the 1,3-dipolar cycloadditions. For this reason, the selection of the reaction conditions is a very complex task and the slow addition of the acrylic system is very important to complete the process. The study of the variation in the structural components of the starting imino ester is performed as well as the expansion of other electron-poor alkenes. The crude products have a purity higher than 90% in most cases without any purification. A plausible mechanism is detailed based on the bibliography and the experimental results. The synthesis of pyroglutamate entities, after the reduction of the imino group and cyclization, is performed in high yields. In addition, the hydrolysis of the imino group, under acidic media, represents a direct access to glutamate surrogates.

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