ASYMMETRIC PALLADIUM-CATALYZED ALKENE CARBOAMINATION REACTIONS FOR THE SYNTHESIS OF CYCLIC SULFAMIDES
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1 AYMMETIC PALLADIUM-CATALYZED ALKEE CABAMIATI EACTI F TE YTEI F CYCLIC ULFAMIDE Chem. Eur. J. 2016, 22, Zachary J. Garlets, Kaia. Parenti, and John P. Wolfe James Johnson Wipf Group Current Literature James Wipf Group Page 1 of 19 3/4/2017
2 2 Alkene Difunctionalization: Carboamination 2 Ethylene is produced from from petroleum and natural gas by thermal cracking. Largest chemical produced organic compound. Alkenes used extensively in the polymer industry. Carboamination or Inexpensive starting materials are rapidly functionalized in a single step Easily accessed heterocycles and amine building blocks (amino acids). James Wipf Group Page 2 of 19 3/4/2017
3 3 Intramolecular Palladium-Catalyzed Carboamination eactions X Y n -B() 2 -Br -Br [Pd] Base X Y n P 1 2 n Boc Boc X 1 1 James Wipf Group Page 3 of 19 3/4/2017
4 4 Intermolecular Carboamination 2 icl 2 (PMe 3 ) 2 (10 mol%) Zn dust (5 eq.) 2 Cu(Tf) 2 (20 mol%) 1,10-phen (25 mol%) 1 1 Mn 2 (255 mol%) 3 1 toluene, 100 C, 12 h 20 examples 21-90% 1 3 Cbz BF 3 K DCE, 105 C, 24 h 35 examples 35-78% Cbz Ph 2 2Ph 2 F mol% Cu(C 3 C) 4 BF 4 (2.5 mol%) PhC, 60 C Ph 1 [Cp*Co(C)I 2 ] (10 mol%) AgbF 6 (20 mol%) CsAc (25 mol%) K 3 P 4 (25 mol%) TFE, 3Å M 40 C, 22 h 17 examples 30-88% 1 s Cat. (20 mol%) 1 2 Fe(phen) 2 3 (bf 6 ) DME, a 3 2 P 4-10 C, 12 h s 17 examples 50-88% Cat. 2:1 dr to >20:1 dr; 87-96% ee 5 6 Cat. 5 mol% 5 Tf 7 4-Me-Ph CCl 3, 2,6-lutadine nm LEDs, rt, 24 h 3 Tf 2 28 examples 35-77% 1.7:1 dr to 16:1 dr 6 7 BF 4 - Mes Ph Cat Br X 1 Pd 2 (dba) 3 (2.5 mol%) CPhos (5 mol%) or L LitBu 2 toluene:t-amyl C, 24 h 20 example 20-94% dr 19:1 to 49:1; % ee X 3 Me PCy 2 L rg. Lett. 2013, 15, ; AC Catal., 2016, 6 (10), pp James Wipf Group Page 4 of 19 3/4/2017
5 5 Wolfe Group Chemistry Boc 1 -Br Pd 2 (dba) 3 (2.5 mol%) ()-iphos-pe (7.5 mol%) atbu toluene, 90 C 23 examples 61-80% 72-94% ee Boc 1 -Br 1 2 PMP -Tf Pd(Ac) 2 (4 mol%) CPhos (10 mol%) LitBu tbu, 82 C, 16 h 9 examples 45-89% 5:1 to 13:1 dr 1 2 PMP C 2 mol% [Pd 2(dba) 3 ] 6 mol% ()-iphos-pe atbu xylenes, 115 C 56-89% (77-95% ee) C C 4 9 Br TM Pd 2 (dba) 3 P(2-furyl) 3 atbu, xylenes tbu 140 C C % >20:1 dr tbu 1) TFA 2) PMBC TM 72% C 4 9 PMP Pd 2 (dba) 3 PCy 3 BF 4 atbu, toluene 110 C 91% >20:1 dr C 4 9 Et PMP C 4 9 C 4 9 James Wipf Group Page 5 of 19 3/4/2017
6 6 Cyclic ulfamides 2 F Active against gram-positive methicillin and vancomycin resistant bacteria Ac 2 Low µm inhibition of norovirusus Me 2 F β-secretase-1 inhibitor Biologically active Enantioselective synthesis usually multi-step starting from amino acids 5 steps 2 2 nly one previous asymmetric metal-catalyzed synthesis rg. Lett., 2013, 15 (4), pp Pd 2 (dba) 3 (2.5 mol%) 10 mol% L toluene, 65 C, 3 h 14 examples, 66-98% 90-93% ee Ph P L Ph James Wipf Group Page 6 of 19 3/4/2017
7 7 Anti-aminopalladation Tf Pd(Ac) 2 (2 mol%) u-phos(5 mol%) LitBu PhCF 3, 100 C 14 examples 51 to 92 % Anti-aminopalladation Chem. Eur. J. 2014, 20, D James Wipf Group Page 7 of 19 3/4/2017
8 8 ptimization of Cyclization with -Tf James Wipf Group Page 8 of 19 3/4/2017
9 9 James Wipf Group Page 9 of 19 3/4/2017
10 10 James Wipf Group Page 10 of 19 3/4/2017
11 11 James Wipf Group Page 11 of 19 3/4/2017
12 12 yn vs Anti-aminopalladation D Ph PhBr Pd(Ac) 2 (2 mol%) X-Phos(5 mol%) atbu toluene, 100 C 47%, 4:1 dr yn-aminopalladation D PhBr Pd(Ac) 2 (2 mol%) C-Phos(5 mol%) atbu PhCF 3, 100 C 90%, >20:1 dr Anti-aminopalladation Ph D Mechanism highly solvent and ligand dependent Chem. Eur. J. 2014, 20, James Wipf Group Page 12 of 19 3/4/2017
13 13 Title Paper -Br Pd 2 (dba) 3 (1 mol%) ()-iphos-pe (5 mol%) atbu xylenes 120 C, 18 h yn-aminopalladation D Chem. Eur. J. 2016, 22, James Wipf Group Page 13 of 19 3/4/2017
14 14 ptimization of Protecting Groups James Wipf Group Page 14 of 19 3/4/2017
15 15 eaction cope Ph Me 2 Me 96% (93:7 er) X = Br 95% (94:6 er) X = I 75% (75:25 er) 85% (95:5 er) 89% (94:6 er) 75% (96:6 er) Me 74% (92:8 er) 74% (90:10 er) Ph 77% (88:12 er) CF 3 69% (90:10 er) F 72% (92:8 er) 58% (68:32 er) 21% (62:38 er) F 3 C 34% (95:5 er) TM 44% (94:6 er) Me James Wipf Group Page 15 of 19 3/4/2017
16 16 Anti-aminopalladation yn-aminopalladation lefin substitution not tolerated James Wipf Group Page 16 of 19 3/4/2017
17 17 Deuterium Labeling tudies EWD groups decrease dr anti-aminopalladation pathway Addition of water (4b) improved yield. o effect on dr or er James Wipf Group Page 17 of 19 3/4/2017
18 18 Deprotection James Wipf Group Page 18 of 19 3/4/2017
19 19 Conclusions Developed enantioselective Pd-catalyzed alkene carboamination with good to high enantio selectivity Example of controlling syn vs anti-aminopalladation Expansion to intermolecular variant? James Wipf Group Page 19 of 19 3/4/2017
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