Palladium/N-heterocyclic carbene catalysed regio and diastereoselective reaction of ketones with allyl reagents via inner-sphere mechanism

Nature Communications

Volumn 7, Issue , 2016, Pages

  Bai, Da Chang ^a   Yu, Fei Le ^a   Wang, Wan Ying ^a   Chen, Di ^a   Li, Hao ^a   Liu, Qing Rong ^a   Ding, Chang Hua ^a   Chen, Bo ^b   Hou, Xue Long ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b Cornell University ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL ALCOHOL; CARBENE; KETONE DERIVATIVE; N HETEROCYCLIC CARBENE; NUCLEOPHILE; PALLADIUM; TRANSITION ELEMENT; UNCLASSIFIED DRUG;

CATALYSIS; CHEMICAL REACTION; EXPERIMENTAL STUDY; KETONE; LIGAND; OXYGEN; PALLADIUM;

ALLYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; COLUMN CHROMATOGRAPHY; COVALENT BOND; CYCLIZATION; DENSITY FUNCTIONAL THEORY; NUCLEOPHILICITY; REACTION ANALYSIS; STEREOCHEMISTRY; SUBSTITUTION REACTION; THIN LAYER CHROMATOGRAPHY; X RAY CRYSTALLOGRAPHY;

EID: 84974574152     PISSN: None     EISSN: 20411723     Source Type: Journal    
DOI: 10.1038/ncomms11806     Document Type: Article

References (58)

1. Trost, B. M., Crawley, M. L. Asymmetric transition-metal-catalyzed allylic alkylations: applications in total synthesis. Chem. Rev. 103, 2921-2944 (2003).
2. Lu, Z., Ma, S. Metal-catalyzed enantioselective allylation in asymmetric synthesis. Angew. Chem. Int. Ed. 47, 258-297 (2008).
3. Ding, C.-H., Hou, X.-L. Transition metal-catalyzed asymmetric allylation. Top Organomet. Chem. 36, 247-285 (2011).
4. Oliver, S., Evens, P. A. Transition-metal-catalyzed allylic substitution reactions: stereoselective construction of a-and b-substituted carbonyl compounds. Synthesis 45, 3179-3198 (2013).
5. You, S.-L., Zhu, X.-Z., Luo, Y.-M., Hou, X.-L., Dai, L.-X. Highly regio-and enantioselective Pd-catalyzed allylic alkylation and amination of monosubstituted allylic acetates with novel ferrocene P,N-ligands. J. Am. Chem. Soc. 123, 7471-7472 (2001).
6. Wei-, T. D., Helmchen, G., Kazmaier, U. Synthesis of amino acid derivatives via enantio-and diastereoselective Pd-catalyzed allylic substitutions with a nonstabilized enolate as nucleophile. Chem. Commun. 12, 1270-1271 (2002).
7. Trost, B. M., Thaisrivongs, D. A. Strategy for employing unstabilized nucleophiles in palladium-catalyzed asymmetric allylic alkylations. J. Am. Chem. Soc. 130, 14092-14093 (2008).
8. Zhang, K., Peng, Q., Hou, X.-L., Wu, Y.-D. Highly enantioselective Palladium-catalyzed alkylation of acyclic amides. Angew. Chem. Int. Ed. 47, 1741-1744 (2008).
9. Trost, B. M., Xu, J.-Y., Schmidt, T. Palladium-catalyzed decarboxylative asymmetric allylic alkylation of enol carbonates. J. Am. Chem. Soc. 131, 18343-18357 (2009).
10. Sha, S.-C., Zhang, J.-D., Carroll, P. J., Walsh, P. J. Raising the pKa Limit of "Soft" nucleophiles in Palladium-catalyzed allylic substitutions: application of diarylmethane pronucleophiles. J. Am. Chem. Soc. 135, 17602-1760 (2013).
11. Mukherjee, S., List, B. Chiral counter anions in asymmetric transition-metal catalysis: highly enantioselective Pd/Brønsted acid-catalyzed direct a-allylation of aldehydes. J. Am. Chem. Soc. 129, 11336-11337 (2007).
12. Jiang, G.-X., List, B. Direct asymmetric a-allylation of aldehydes with simple allylic alcohols enabled by the concerted action of three different catalysts. Angew. Chem. Int. Ed. 50, 9471-9474 (2011).
13. Negishi, E. Handbook of Organopalladium Chemistry For Organic Synthesis (Wiley, 2002).
14. Bäckvall, J.-E., Nordberg, R. E., Björkman, E. E., Moberg, C. Stereochemistry of nucleophilic attack on p-allylpalladium complexes. Evidence for cismigration of acetate from palladium to carbon. J. Chem. Soc. Chem. Commun. 943-944 (1980).
15. Hayashi, T., Iwamura, H., Naito, M., Matsumoto, Y., Uozumi, Y. Catalytic asymmetric reduction of allylic esters with formic acid catalyzed by Pd-MOP complexes. J. Am. Chem. Soc. 116, 775-776 (1994).
16. Nakamura, H., Bao, M., Yamamoto, Y. The Fate of Bis(Z3-allyl)palladium complexes in the presence of aldehydes (or imines) and allylic chlorides: stille coupling versus allylation of aldehydes (or imines). Angew. Chem. Int. Ed. 40, 3208-3210 (2001).
17. Stokes, B. J., Opra, S. M., Sigman, M. S. Palladium-catalyzed allylic crosscoupling reactions of primary and secondary homoallylic electrophiles. J. Am. Chem. Soc. 134, 11408-11411 (2012).
18. Li, Y.-X. et al. A Pd(0)-catalyzed direct dehydrative coupling of terminal alkynes with allylic alcohols to access 1,4-enynes. J. Am. Chem. Soc. 135, 12536-12539 (2013).
19. Bai, D.-C., Wang, W.-Y., Ding, C.-H., Hou, X.-L. Kinetic resolution of unsymmetrical acyclic allyl carbonates using trimethylsilyl cyanide via Palladium-catalyzed asymmetric allylic alkylation. Synlett 26, 1510-1514 (2015).
20. Xiang, S.-H., Hoang, K. L. M., He, J.-X., Tan, Y.-J., Liu, X.-W. Reversing the stereoselectivity of a palladium-catalyzed O-Glycosylation through an innersphere or outer-sphere pathway. Angew. Chem. Int. Ed. 54, 604-607 (2015).
21. Méndez, M., Cuerva, J. M., Gómez-Bengoa, E., Cárdenas, D. J., Echavarren, A. M. Intramolecular coupling of allyl carboxylates with allylstannanes and allylsilanes: a new type of reductive elimination reaction? Chem. Eur. J. 8, 3620-3628 (2002).
22. Cárdenas, D. J., Echavarren, A. M. Mechanistic aspects of C-C bond formation involving allylpalladium complexes: the role of computational studies. New J. Chem. 28, 338-347 (2004).
23. Luzung, M. R., Lewis, C. A., Baran, P. S. Direct, chemoselective N-tert-prenylation of indoles by C-H functionalization. Angew. Chem. Int. Ed. 48, 7025-7029 (2009).
24. Perez-Rodriguez, M. et al. A DFT study of the effect of the ligands in the reductive elimination from Palladium bis(allyl) complexes. Organometallics 29, 4983-4991 (2010).
25. Keith, J. A. et al. The inner-sphere process in the enantioselective Tsuji allylation reaction with (S)-t-Bu-phosphinooxazoline ligands. J. Am. Chem. Soc. 129, 11876-11877 (2007).
26. Enquist, Jr. J. A., Stoltz, B. M. The total synthesis of (-)-cyanthiwigin F by means of double catalytic enantioselective alkylation. Nature 453, 1228-1231 (2008).
27. Sherden, N. H., Behenna, D. C., Virgil, S. C., Stoltz, B. M. Unusual allylpalladium carboxylate complexes: identification of the resting state of catalytic enantioselective decarboxylative allylic alkylation reactions of ketones. Angew. Chem. Int. Ed. 48, 6840-6843 (2009).
28. Zhang, P., Brozek, L. A., Morken, J. P. Pd-catalyzed enantioselective allyl-allyl cross-coupling. J. Am. Chem. Soc. 132, 10686-10688 (2010).
29. Zhang, P., Le, H., Kyne, R. E., Morken, J. P. Enantioselective construction of all-carbon quaternary centers by branch-selective Pd-catalyzed allyl-allyl crosscoupling. J. Am. Chem. Soc. 133, 9716-9719 (2011).
30. Brozek, L. A., Ardolino, M. J., Morken, J. P. Diastereocontrol in asymmetric allyl-allyl cross-coupling: stereocontrolled reaction of prochiral allylboronates with prochiral allyl chlorides. J. Am. Chem. Soc. 133, 16778-16781 (2011).
31. Ardolino, M. J., Morken, J. P. Congested C-C bonds by Pd-catalyzed enantioselective allyl-allyl cross-coupling, a mechanism-guided solution. J. Am. Chem. Soc. 136, 7092-7100 (2014).
32. Ardolino, M. J., Morken, J. P. Construction of 1,5-enynes by stereospecific Pd-catalyzed allyl-propargyl cross-couplings. J. Am. Chem. Soc. 134, 8770-8773 (2012).
33. Chen, J.-P., Peng, Q., Lei, B.-L., Hou, X.-L., Wu, Y.-D. Chemo-and regioselectivity-tunable Pd-catalyzed allylic alkylation of imines. J. Am. Chem. Soc. 133, 14180-14183 (2011).
34. Keith, J. A. et al. The reaction mechanism of the enantioselective Tsuji allylation: inner-sphere and outer-sphere pathways, internal rearrangements, and asymmetric C-C Bond formation. J. Am. Chem. Soc. 134, 19050-19060 (2012).
35. Nolan, S. P. N-Heterocyclic Carbenes (Wiley-VCH, 2014).
36. Nicolaou, K. C., Vourloumis, D., Winssinger, M., Baran, P. S. The art and science of total synthesis at the dawn of the twenty-first century. Angew. Chem. Int. Ed. 39, 44-122 (2000).
37. Gaich, T., Baran, P. S. Aiming for the ideal synthesis. J. Org. Chem. 75, 4657-4673 (2010).
38. Newman, D. J., Cragg, G. M. Natural products as sources of new drugs over the 30 years from 1981 to 2010. J. Nat. Prod. 75, 311-335 (2012).
39. Wheeler, S. E. Understanding substituent effects in noncovalent interactions involving aromatic rings. Acc. Chem. Res. 46, 1029-1038 (2013).
40. Wheeler, S. E., Bloom, J. W. G. Toward a more complete understanding of noncovalent interactions involving aromatic rings. J. Phys. Chem. A. 118, 6133-6147 (2014).
41. Seguin, T. J., Lu, T.-X., Wheeler, S. E. Enantioselectivity in catalytic asymmetric fischer indolizations hinges on the competition of p-stacking and CH/p interactions. Org. Lett. 17, 3066-3069 (2015).
42. Roscales, S., Rincón, Á ngela., Buxaderas, E., Csákÿ, A. G. Trifluoroacetic anhydride-catalyzed conjugate addition of boronic acids to a,b-unsaturated ketones. Tetrahedron. Lett. 53, 4721-4724 (2012).
43. Chong, J. M., Shen, L. X., Taylor, N. J. Asymmetric conjugate addition of alkynylboronates to enones. J. Am. Chem. Soc. 122, 1822-1823 (2000).
44. Krause, N., Hoffmann-Roder, A. Recent advances in catalytic enantioselective Michael additions. Synthesis 2, 171-196 (2001).
45. Hayashi, T., Yamasaki, K. Rhodium-catalyzed asymmetric 1,4-addition and its related asymmetric reactions. Chem. Rev. 103, 2829-2844 (2003).
46. Tsogoeva, S. B. Recent advances in asymmetric organocatalytic 1,4-conjugate additions. Eur. J. Org. Chem. 11, 1701-1716 (2007).
47. Endo, K., Ogawa, M., Shibata, T. Multinuclear catalyst for copper-catalyzed asymmetric conjugate addition of organozinc reagents. Angew. Chem. Int. Ed. 49, 2410-2413 (2010).
48. Nishimura, T., Guo, X.-X., Uchiyama, N., Katoh, T., Hayashi, T. Steric tuning of silylacetylenes and chiral phosphine ligands for Rhodium-catalyzed asymmetric conjugate alkynylation of enones. J. Am.Chem. Soc. 130, 1576-1577 (2008).
49. Guo, X. T., Shen, J., Sha, F., Wu, X.-Y. Highly enantioselective Michael addition of nitroalkanes to enones and its application in syntheses of (R)-Baclofen and (R)-Phenibut. Synthesis 47, 2063-2072 (2015).
50. Diver, S. T., Giessert, A. J. Enyne metathesis (enyne bond reorganization). Chem. Rev. 104, 1317-1382 (2004).
51. Blanco-Urgoiti, J., Anõrbe, L., Pérez-Serrano, L., Domnguez, G., Pérez-Castells, J. The Pauson-Khand reaction, a powerful synthetic tool for the synthesis of complex molecules. Chem. Soc. Rev. 33, 32-42 (2004).
52. Mukai, C., Kim, J. S., Sonobe, H., Hanaoka, M. Stereocomplementary construction of optically active bicyclo[4.3.0]nonenone derivatives. J. Org. Chem. 64, 6822-6832 (1999).
53. Hiroi, K., Watanabe, T., Kawagishi, R., Abe, I. Catalytic use of chiral phosphine ligands in asymmetric Pauson-Khand reactions. Tetrahedron. Asymmetry. 11, 797-808 (2000).
54. Dolhem, F., Lièvre, C., Demailly, G. Synthesis of carbohydrate-derived enynes and subsequent metathesis to yield polyhydroxylated 1-vinylcycloalkenes. Eur. J. Org. Chem. 12, 2336-2342 (2003).
55. Funel, J.-A., Prunet, J. Enyne versus diene RCM in the synthesis of cyclopentene derivatives toward the A ring of FR182877. J. Org. Chem. 69, 4555-4558 (2004).
56. Xue, Z. J., Chen, P., Peng, S. Y., Li, Y. C. Synthesis and determination of absolute configuration of tetracetate 4a-carba-D-xylofuranoside. Tetrahedron 62, 199-204 (2006).
57. Krishna, P. R., Alivelu, M. Stereoselective synthesis of aminocyclitol moieties of trehazolin and trehalostatin via enyne metathesis protocol. Tetrahedron Lett. 51, 6265-6267 (2010).
58. Patil, M., Thiel, W. Origin of selectivity of Tsuji-Trost allylic alkylation of lactones: highly ordered transition states with lithium-containing enolates. Chem. Eur. J. 18, 10408-10418 (2012).