Catalytic Asymmetric [4+1] Annulation of Sulfur Ylides with Copper Allenylidene Intermediates. Reporter: Jie Wang Checker: Shubo Hu Date: 2016/08/02
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1 Catalytic Asymmetric [4+1] Annulation of Sulfur Ylides with Copper Allenylidene Intermediates Reporter: Jie Wang Checker: Shubo Hu Date: 2016/08/02 Xiao, W.-J. et al. J. Am. Chem. Soc. 2016, 138, 8360.
2 Contents 1 Introduction 2 Formal [3+2] Cycloaddition with Ru-Allenylidene 3 4 Formal [4+1] Cycloaddition with Cu-Allenylidene Formal [3+2] Cycloaddition with Cu-Allenylidene 5 Summary 2
3 Introduction Metal-associated dipolar intermediates TBS [Pd] u [M] CR u [M] u type-i M=RhandAu type-Ⅱ type-iii Trost, B.M.et al. J. Am. Chem. Soc. 2012, 134, Doyle, M. P. et al. J. Am. Chem. Soc. 2016, 138, 44. 3
4 Ruthenium Allenylidene C 2 R C 2 R + X Ar H X= or Ru catalyst racemic R 2 C R 2 C X Ar up to 98% yield ishibayashi, Y. et al. Angew. Chem. Int. Ed. 2013, 52,
5 Condition ptimization entry cat. 3 2a (eq.) 4a yield (%) (trans:cis) 1 3a 5 88 (2:1) 2 3a 3 67 (2:1) 3 3b 5 73 (2:1) 4 3c 5 51 (2:1) 5
6 Substrate Scope entry R Ar 4 yield (%) (trans:cis) 1 Me 88 (2:1) 2 Me 4-MeC 6 H 4 87 (2:1) 3 Me 4-MeC 6 H 4 81 (2:1) 4 Me 4-FC 6 H 4 75 (2:1) 5 Me 3-MeC 6 H 4 80 (2:1) 6 Me 2-MeC 6 H 4 61 (1:1) 7 Et 74 (2:1) 8 Et 4-MeC 6 H 4 70 (2:1) 6
7 Substrate Scope entry R Ar 6 yield (%) (trans:cis) 1 Me 88 (1:50) 2 Me 4-MeC 6 H 4 52 (1:8) 3 Me 4-MeC 6 H 4 63 (1:20) 4 Me 4-FC 6 H 4 86 (1:50) 5 Me 3-MeC 6 H 4 80 (1:30) 6 Me 2-naphthyl 76 (1:50) 7 Et 77 (1:50) 8 Et 4-ClC 6 H 4 90 (1:50) 7
8 Proposed Mechanism 8
9 Copper Allenylidene + Cu(Tf) 2 (10 mol%) L (11 mol%) S i Pr 2 Et (1.2 eq.) MeH, rt in-situ generated up to 99% yield up to 98% ee >95:5 dr Xiao, W.-J. et al. J. Am. Chem. Soc. 2016, 138,
10 Ligand effects 10
11 Condition ptimization Cu(Tf) 2 (10 mol%) R 1 L4 (11 mol%) + S i Pr R2 2 Et (1.2 eq.) solvent, rt 1a 2 3aa >95:5 dr entry solvent 2 (R 1 /R 2 ) yield (%) ee (%) 1 MeH CH 3 /CH THF CH 3 /CH Dioxane CH 3/CH CH 3 C CH 3 /CH Toluene CH 3 /CH CH 2 Cl 2 CH 3 /CH THF CH 3 / THF -(CH 2 )
12 Condition ptimization entry base T ( o C) Cu yield (%) ee (%) 1 i Pr 2 Et rt Cu(Tf) rt Cu(Tf) DABC rt Cu(Tf) i Pr 2 Et 0 Cu(Tf) i Pr 2 Et -10 Cu(Tf) i Pr 2 Et 0 Cu(CH 3 C) 4 BF i Pr 2 Et 0 CuI i Pr 2 Et 0 Cu(Tf)
13 Substrate Scope entry R yield (%) ee (%) 1 C 6 H C 6 H FC 6 H MeC 6 H BrC 6 H FC 6H benzofuryl methyl cyclohexyl
14 Substrate Scope R 1a-h + S MeS 3 4a Cu(Tf) 2 (10 mol%) L4 (11 mol%) i Pr 2 Et (3.2 eq.) THF, 0 o C R 3: >95:5 dr Br Me 3aa: 94% yield, 95% ee 3ba: 97% yield, 90% ee 3ca: 99% yield, 91% ee 3da: 95% yield, 81% ee F Cl 3ea: 99% yield, 95% ee F 3 C 3fa: 96% yield, 94% ee 3ga: 93% yield, 80% ee F 3ha: 82% yield, 88% ee 14
15 Substrate Scope 15
16 Proposed Mechanism 16
17 Possible Mode Two Copper: Cooperative Catalysis R R R Cu Cu R (X - ) 2 Re-favored Cu H Cu S H X=TforPF 6 results of Gamasa and ishibayashi Maarseveen' model Y. ishibayashi et al. J. Am. Chem. Soc. 2015, 137,
18 Synthetic Transformation 18
19 Copper Allenylidene entry R T yield (%) ee (%) 1 H RT SiMe 3 RT SiEt 3 RT Si t BuMe 2 RT SiMe Hu, X.-P. et al. Angew. Chem. Int. Ed. 2016, 55,
20 Condition ptimization 20
21 Substrate Scope entry R 1 yield (%) ee (%) MeC 6 H MeC 6 H FC 6 H ClC 6 H ClC 6H Furyl Et cyclohexyl
22 Substrate Scope entry R yield (%) ee (%) 1 H Me Me Me Br Br H CH H
23 Proposed Mechanism 23
24 Summary ishibayashi, Y. et al. Angew. Chem. Int. Ed. 2013, 52, in-situ generated S L4 (11 mol%) i Pr 2 Et (3.2 eq.) Cu(Tf) 2 (10 mol%) up to 99% yield up to 98% ee >95:5 dr Xiao, W.-J. et al. J. Am. Chem. Soc. 2016, 138, Hu, X.-P. et al. Angew. Chem. Int. Ed. 2016, 55, 5014.
25 Transition-metal-catalyzed cycloaddition reactions have been the focus of extensive study because of their fundamental importance in organic, medicinal, and materials chemistry. Many reactions proceed via metalassociated dipolar intermediates, which involve two independent reaction centers: one acts as an electrophile, and the other acts as a nucleophile. For example, various nucleophile-containing π-allyl Pd complexes and metalloenolcarbenes have been widely applied in transition-metalcatalyzed cycloadditions. To expand this cycloaddition chemistry, we applied asymmetric catalysis by earth abundant metals to achieve the first example of formal [4+1] cycloaddition of copper allenylidene dipolar intermediates with high reaction yields and enantio- and diastereoselectivities. 25
26 In conclusion, we developed a copper catalyzed asymmetric formal [4+1] cycloaddition for the first time by trapping copper allenylidene dipolar intermediates with sulfur ylides. Thus, a new approach to chiral indoline products and related cycloadducts with high reaction yields and stereoselectivities was explored. Mechanistic studies suggest that this reaction is a sequence process that involves decarboxylative propargylation/s 2 reactions promoted by dinuclear copper complexes. Further studies with this type of metal-associated dipolar intermediate are currently in progress. 26
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