trans-3,4-Disubstituted pyrrolidines by 1,3-dipolar cycloaddition: enantioselective approaches and their limitations

Karlsson, Staffan; Han, Fusen; Högberg, Hans‐Erik; Caldirola, P.

doi:10.1016/s0957-4166(99)00244-x

Cited by 34 publications

(13 citation statements)

References 19 publications

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“…In some cases we have observed selectivity of up to 5 to 1 in this addition. 28 The stereochemistry at the -carbon was determined by Xray of 53. Since there was interest in screening both diastereomers, the conditions were altered in such way that a $ 1:1 mixture could be obtained.…”

Section: Entries 18mentioning

confidence: 99%

Synthesis of phosphine containing amino acids: Utilization of peptide synthesis in ligand design

et al. 2005

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Combinatorial chemistry has recently burst on the scene as a valuable tool for the discovery of new drug candidates. The ability to synthesize hundreds of compounds for screening is a useful complement to rational drug design. There are many similarities between the design of new therapeutic agents and the development of new asymmetric ligands, the most important of which is the limitation of a rational design strategy. For this reason a program was begun that would allow the use of combinatorial technology in the development of new ligands for transition metal catalyzed asymmetric reactions. Because of the large number of catalytic reactions they are involved in the system was based around phosphine ligands. This paper reports the synthesis of phosphine derivatives of alanine, proline, and the aromatic amino acids tyrosine and hydroxyphenylglycine. Examples of the use of these amino acids in the synthesis of peptides possessing helical and beta-turn secondary structures are presented. Metal complexes of these peptide-based ligands are used in hydrogenation and alkylation reactions.

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Section: Entries 18mentioning

confidence: 99%

Synthesis of phosphine containing amino acids: Utilization of peptide synthesis in ligand design

et al. 2005

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“…) 1 H NMR (500 MHz, DMSO-d6) δ 9,66 (s, 1H), 6,91 (s, 2H), 6,83 (s, 2H), 3,71 (s, 6H), 3,61 (s, 3H), 3,57 (s, 1H), 2,31 (s, 6H), 2,18 (s, 3H), 1,67 (s, 3H), 1,40 (s, 9H); 13 C NMR (126 MHz, DMSO-d6) δ 175,9, 165,2, 164,3, 152,5, 138,9, 135,9, 134,4, 133,9, 132,1, 128,8, 99,2, 82,5, 60,1, 55,8, 48,7, 43,5, 27,6, 20,6, 20, ), 3,99 (q, J = 7,1 Hz, 2H), 3,92 (qt, J = 6,7, 3,3 Hz, 2H), 3,77 (s, 3H), 3,75 (s, 3H), 1,58 (s, 3H), 1,53 (s, 3H), 1,42 (s, 3H), 1,37 (s, 3H); 13 C NMR (126 MHz, DMSO-d6) δ diasztereomer keverék : 172,4, 172,3, 168,1, 167,3, 167,3, 167,2, 159,2, 159,1, 139,2, 139,2, 136,2, 135,1, 129,8, 129,7, 128,3, 128,2, 127,6, 127,5, 126,9, 126,8, 120,6, 120,0, 119,2, 118,0, 113,0, 112,5, 61,8, 61,3, 55,3, 55,3, 50,6, 49,7, 42,5, 42,5, 15,7, 14,1, 13,8, 13 1H), 1,49 (s, 3H), 1,30 (s, 9H), 0,95 (t, J = 6,9 Hz, 3H); 13 C NMR (126 MHz, DMSO-d6) δ 172,1,166,6,166,3,136,8,134,5,131,9,129,5,128,3,128,1,127,9,126,7,61,5,52,5,52,4,51,2,35,2,28,4,…”

Section: (±)-Terc-butil-transz-3-metil-3-((345-trimetoxifenil)-karbamoil)-1-(246trimetilbenzoil)-aziridin-2-karboxilát ((±)-281{32}mentioning

confidence: 99%

“…) 1 H NMR (500 MHz, DMSO-d6) δ 7,99 (d, J = 7,1 Hz, 2H), 7,63 (t, J = 7,4 Hz, 1H), 7,51 (t, J = 7,9 Hz, 2H), 7,35 (d, J = 7,5 Hz, 2H), 7,27 -7,22 (m, 2H), 7,22 -7,15 (m, 1H), 7,08 (s, 1H), 3,88 -3,74 (m, 2H), 3,28 -3,10 (m, 2H), 1,42 (s, 3H), 1,23 (d, J = 2,7 Hz, 9H), 0,82 (t, J = 7,2 Hz, 3H); 13 C NMR (126 MHz, DMSO-d6) δ 172,6,166,8,166,2,135,9,133,8,133,1,129,5,128,7,128,4,127,9,126,6,61,0,53,2,50,9,50,6,33,9,28,1,14,8,13 13 C NMR (126 MHz, DMSO-d6) δ 177,4,164,6,138,1,134,4,133,…”

Section: (±)-Etil-cisz-1-benzoil-2-benzil-3-(terc-butilkarbamoil)-3-metilaziridin-2-karboxilát ((±)-282{36}mentioning

confidence: 99%

“…) 1 H NMR (500 MHz, DMSO-d6) δ 7,52 (s, 1H), 7,45 -7,37 (m, 4H), 7,37 -7,30 (m, 1H), 7,31 -7,22 (m, 4H), 7,23 -7,17 (m, 1H), 3,79 (s, 1H), 3,25 (d, J = 15,1 Hz, 1H), 2,44 (d, J = 15,2 Hz, 1H), 1,65 (s, 3H), 1,22 (s, 9H); 13 C NMR (126 MHz, DMSO-d6) δ 180,2, 166,2, 137,2, 134,6,129,3,128,3,128,2,127,9,127,8,126,7,55,4,51,4,46,7,32,6,28,3,24 (±)-281{43}) 1 H NMR (500 MHz, DMSO-d6) δ 7,61 (d, J = 7,8 Hz, 1H), 7,39 -7,29 (m, 4H), 7,27 (t, J = 6,6 Hz, 1H), 7,12 -7,02 (m, 3H), 6,88 (d, J = 6,9 Hz, 2H), 6,81 (s, 2H), 4,42 (s, 1H), 3,48 (d, J = 16,1 Hz, 1H), 3,46 -3,37 (m, 1H), 2,76 (d, J = 16,1 Hz, 1H), 2,32 (s, 6H), 2,17 (s, 3H), 1,55 (d, J = 13,1 Hz, 1H), 1,52 -1,41 (m, 3H), 1,61 -1,51 (m, 1H), 1,52 -1,41 (m, 3H), 1,39 -1,29 (m, 1H), 1,20 -1,05 (m, 2H), 1,06 -0,90 (m, 3H); 13 karboxamid ((±)-281{44}) 1 H NMR (500 MHz, DMSO-d6) δ 10,13 (s, 1H), 7,48 (d, J = 7,7 Hz, 2H), 7,44 (t, J = 7,4 Hz, 2H), 7,42 -7,34 (m, 1H), 7,35 -7,26 (m, 4H), 7,27 -7,15 (m, 4H), 7,12 (d, J = 7,5 Hz, 2H), 7,07 (s, 2H), 4,02 (s, 1H), 3,75 (s, 6H), 3,62 (s, 3H), 3,60 -3,49 (m, 2H), 3,30 (s, 9H), 3,20 (d, J = 6,7 Hz, 2H); 13 C NMR (126 MHz, DMSO-d6) δ 181,0, 166,3, 152,7, 137,0, 135,4,134,4,134,2,…”

Section: (±)-Transz-1-acetil-2-benzil-n-(terc-butil)-3-fenilaziridin-2-karboxamid ((±)-281{42}mentioning

confidence: 99%

“…1 H NMR (500 MHz, Kloroform-d) δ 7,74 (d, J = 7,5 Hz, 2H), 7,57 (d, J = 7,6 Hz, 2H), 7,49 (t, J = 7,5 Hz, 2H), 7,42 (t, J = 7,4 Hz, 1H), 7,33 (d, J = 8,2 Hz, 2H), 7,22 (t, J = 7,6 Hz, 2H), 7,14 (t, J = 7,3 Hz, 1H), 7,01 (d, J = 8,2 Hz, 2H), 3,88 (s, 3H), 3,49 (s, 3H), 13 terc-Butil 2-izopropil-1,5-dimetil-1H-imidazol-4-karboxilát (361) 1 H NMR (500 MHz, Kloroform-d) δ 3,45 (s, 3H), 2,98 (hept, J = 6,9 Hz, 1H), 2,44 (s, 3H), 1,58 (s, 9H), 1,34 (d, J = 6,9 Hz, 6H), 13 C NMR (126 MHz, Kloroform-d) δ 163,3,152,4,134,3,128,6,80,1,30,0,28,4,26,6,20,9,10,5; HRMS (ESI) 239,1753 [M+H] + (kalkulált: 239,1755).…”

Section: (±)-Transz-1-acetil-2-benzil-n-(terc-butil)-3-fenilaziridin-2-karboxamid ((±)-281{42}mentioning

confidence: 99%

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trans-3,4-Disubstituted pyrrolidines by 1,3-dipolar cycloaddition: enantioselective approaches and their limitations

Cited by 34 publications

References 19 publications

Synthesis of phosphine containing amino acids: Utilization of peptide synthesis in ligand design

Synthesis of phosphine containing amino acids: Utilization of peptide synthesis in ligand design

2H-Azirinek új típusú reakciói

Catalytic Generation of Ammonium Enolates and Related Tertiary Amine‐Derived Intermediates: Applications, Mechanism, and Stereochemical Models ( n ?→?π ^* )

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trans-3,4-Disubstituted pyrrolidines by 1,3-dipolar cycloaddition: enantioselective approaches and their limitations

Cited by 34 publications

References 19 publications

Synthesis of phosphine containing amino acids: Utilization of peptide synthesis in ligand design

Synthesis of phosphine containing amino acids: Utilization of peptide synthesis in ligand design

2H-Azirinek új típusú reakciói

Catalytic Generation of Ammonium Enolates and Related Tertiary Amine‐Derived Intermediates: Applications, Mechanism, and Stereochemical Models ( n ?→?π * )

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Catalytic Generation of Ammonium Enolates and Related Tertiary Amine‐Derived Intermediates: Applications, Mechanism, and Stereochemical Models ( n ?→?π ^* )