Asymmetric transformations via C–C bond cleavage

Topics in Current Chemistry

Volumn 346, Issue , 2014, Pages 163-194

  Souillart, Laetitia ^a   Parker, Evelyne ^a   Cramer, Nicolai ^a  

^a EPFL   (Switzerland)

Author keywords

Asymmetric catalysis; C C cleavage; Ligands; Oxidative insertion; Palladium; Rhodium; Strain release; Carbon elimination

Indexed keywords

EID: 84921467809     PISSN: 03401022     EISSN: None     Source Type: Book Series    
DOI: 10.1007/128_2013_505     Document Type: Article

References (90)

1. Jun C-H (2004) Transition metal-catalyzed carbon-carbon bond activation. Chem Soc Rev 33 (9): 610-618. doi: 10. 1039/b308864m.
2. Muzart J (2005) Palladium-catalysed reactions of alcohols. Part D: rearrangements, carbonylations, carboxylations and miscellaneous reactions. Tetrahedron 61(40): 9423-9463. doi: 10. 1016/j. tet. 2005. 06. 103.
3. Murakami M, Makino M, Ashida S, Matsuda T (2006) Construction of carbon frameworks through beta-carbon elimination mediated by transition metals. Bull Chem Soc Jpn 79 (9): 1315-1321. doi: 10. 1246/bcsj. 79. 1315.
4. Park YJ, Park J-W, Jun C-H (2008) Metal-organic cooperative catalysis in C-H and C-C bond activation and its concurrent recovery. Acc Chem Res 41(2): 222-234. doi: 10. 1021/ar700133y.
5. Khoury PR, Goddard JD, Tam W (2004) Ring strain energies: substituted rings, norbornanes, norbornenes and norbornadienes. Tetrahedron 60(37): 8103-8112. doi: 10. 1016/j. tet. 2004. 06. 100.
6. Russo A, De Fusco C, Lattanzi A (2012) Organocatalytic asymmetric oxidations with hydrogen peroxide and molecular oxygen. ChemCatChem 4(7): 901-916. doi: 10. 1002/cctc. 201200139.
7. Leisch H, Morley K, Lau PCK (2011) Baeyer-Villiger monooxygenases: more than just green chemistry. Chem Rev 111(7): 4165-4222. doi: 10. 1021/cr1003437.
8. Bolm C (2007) Asymmetric Baeyer-Villiger. In: Asymmetric synthesis-the essentials. Wiley-VCH, Weinheim, pp 62-66.
9. ten Brink GJ, Arends IWCE, Sheldon RA (2004) The Baeyer-Villiger reaction: new developments toward greener procedures. Chem Rev 104(9): 4105-4124. doi: 10. 1021/cr030011l.
10. Kirmse W (2002) 100 years of the Wolff rearrangement. Eur J Org Chem 2002 (14): 2193-2256. doi: 10. 1002/1099-0690(200207)2002: 14<2193:: aid-ejoc2193>3. 0. co; 2-d.
11. Seiser T, Saget T, Tran DN, Cramer N (2011) Cyclobutanes in catalysis. Angew Chem Int Ed 50(34): 7740-7752. doi: 10. 1002/anie. 201101053.
12. Seiser T, Cramer N (2009) Enantioselective metal-catalyzed activation of strained rings. Org Biomol Chem 7(14): 2835-2840. doi: 10. 1039/b904405a.
13. Winter C, Krause N (2009) Rhodium(I)-catalyzed enantioselective C-C bond activation. Angew Chem Int Ed 48(14): 2460-2462. doi: 10. 1002/anie. 200805578.
14. Murakami M (2010) Rhodium-catalyzed restructuring of carbon frameworks. Chem Rec 10(5): 326-331. doi: 10. 1002/tcr. 201000023.
15. Murakami M, Matsuda T (2011) Metal-catalysed cleavage of carbon-carbon bonds. Chem Commun 47(4): 1100-1105. doi: 10. 1039/c0cc02566f.
16. Huffman MA, Liebeskind LS, Pennington WT (1990) Synthesis of metallacyclopentenones by insertion of rhodium into cyclobutenones. Organometallics 9(8): 2194-2196. doi: 10. 1021/om00158a009.
17. Huffman MA, Liebeskind LS (1990) Insertion of (. eta. 5-indeny)cobalt(I) into cyclobutenones: the first synthesis of phenols from isolated vinylketene complexes. J Am Chem Soc 112 (23): 8617-8618. doi: 10. 1021/ja00179a075.
18. Huffman MA, Liebeskind LS (1991) Nickel(0)-catalyzed synthesis of substituted phenols from cyclobutenones and alkynes. J Am Chem Soc 113(7): 2771-2772. doi: 10. 1021/ja00007a072.
19. Huffman MA, Liebeskind LS, Pennington WT (1992) Reaction of cyclobutenones with low-valent metal reagents to form. eta. 4-and. eta. 2-vinylketene complexes. Reaction of. eta. 4-vinylketene complexes with alkynes to form phenols. Organometallics 11(1): 255-266. doi: 10. 1021/om00037a047.
20. Kondo T, Taguchi Y, Kaneko Y, Niimi M, Mitsudo TA (2004) Ru-and Rh-catalyzed C-C bond cleavage of cyclobutenones: reconstructive and selective synthesis of 2-pyranones, cyclopentenes, and cyclohexenones. Angew Chem Int Ed 43(40): 5369-5372. doi: 10. 1002/anie. 200461002.
21. Kondo T, Mitsudo TA (2005) Ruthenium-catalyzed reconstructive synthesis of functional organic molecules via cleavage of carbon-carbon bonds. Chem Lett 34(11): 1462-1467.
22. Kondo T, Niimi M, Nomura M, Wada K, Mitsudo TA (2007) Rhodium-catalyzed rapid synthesis of substituted phenols from cyclobutenones and alkynes or alkenes via C-C bond cleavage. Tetrahedron Lett 48(16): 2837-2839, http://dx. doi. org/10. 1016/j. tetlet. 2007. 02. 091.
23. Kondo T (2008) On inventing catalytic reactions via ruthena-or rhodacyclic intermediates for atom economy. Synlett 5: 629-644. doi: 10. 1055/s-2008-1042807.
24. Xu T, Dong G (2012) Rhodium-catalyzed regioselective carboacylation of olefins: a C-C bond activation approach for accessing fused-ring systems. Angew Chem Int Ed 51(30): 7567-7571. doi: 10. 1002/anie. 201202771.
25. Xu T, Ko HM, Savage NA, Dong G (2012) Highly enantioselective Rh-catalyzed carboacylation of olefins: efficient syntheses of chiral poly-fused rings. J Am Chem Soc 134 (49): 20005-20008. doi: 10. 1021/ja309978c.
26. Miura M, Satoh T (2005) Catalytic processes involving β-carbon elimination. In: Tsuji J (ed) Palladium in organic synthesis, vol 14, Topics in organometallic chemistry. Springer, Berlin, Heidelberg, pp 1-20. doi: 10. 1007/b104133.
27. Cramer N, Seiser T (2011) Beta-carbon elimination from cyclobutanols: a clean access to alkylrhodium intermediates bearing a quaternary stereogenic center. Synlett 4: 449-460. doi: 10. 1055/s-0030-1259536.
28. Murakami M, Amii H, Ito Y (1994) Selective activation of carbon-carbon bonds next to a carbonyl group. Nature 370(6490): 540-541. doi: 10. 1038/370540a0.
29. Matsuda T, Fujimoto A, Ishibashi M, Murakami M(2004) Eight-membered ring formation via olefin insertion into a carbon-carbon single bond. Chem Lett 33(7): 876-877.
30. Murakami M, Itahashi T, Ito Y (2002) Catalyzed intramolecular olefin insertion into a carbon_carbon single bond. J Am Chem Soc 124(47): 13976-13977. doi: 10. 1021/ja021062n.
31. Kumar P, Zhang K, Louie J (2012) An expeditious route to eight-membered heterocycles by nickel-catalyzed cycloaddition: low-temperature C sp2-C sp3 bond cleavage. Angew Chem Int Ed 51(34): 8602-8606. doi: 10. 1002/anie. 201203521.
32. Ishida N, Yuhki T, Murakami M (2012) Synthesis of enantiopure dehydropiperidinones from α-amino acids and alkynes via azetidin-3-ones. Org Lett 14(15): 3898-3901. doi: 10. 1021/ol3016447.
33. Ashida S, Murakami M (2008) Nickel-catalyzed 4+2+2-type annulation reaction of cyclobutanones with diynes and enynes. Bull Chem Soc Jpn 81(7): 885-893. doi: 10. 1246/bcsj. 81. 885.
34. Murakami M, Ashida S, Matsuda T (2006) Eight-membered ring construction by [4+2+2] annulation involving β-carbon elimination. J Am Chem Soc 128(7): 2166-2167. doi: 10. 1021/ja0552895.
35. Murakami M, Ashida S, Matsuda T (2005) Nickel-catalyzed intermolecular alkyne insertion into cyclobutanones. J Am Chem Soc 127(19): 6932-6933. doi: 10. 1021/ja050674f.
36. Murakami M, Ashida S (2006) Nickel-catalysed intramolecular alkene insertion into cyclobutanones. Chem Commun 44: 4599-4601. doi: 10. 1039/b611522e.
37. Liu L, Ishida N, Murakami M (2012) Atom-and step-economical pathway to chiral benzobicyclo[2. 2. 2]octenones through carbon-carbon bond cleavage. Angew Chem Int Ed 51(10): 2485-2488. doi: 10. 1002/anie. 201108446.
38. Matsuda T, Shigeno M, Makino M, Murakami M (2006) Enantioselective C-C bond cleavage creating chiral quaternary carbon centers. Org Lett 8(15): 3379-3381. doi: 10. 1021/ol061359g.
39. Matsuda T, Shigeno M, Murakami M (2007) Asymmetric synthesis of 3, 4-dihydrocoumarins by rhodium-catalyzed reaction of 3-(2-hydroxyphenyl)cyclobutanones. J Am Chem Soc 129 (40): 12086-12087. doi: 10. 1021/ja075141g.
40. Nishimura T, Ohe K, Uemura S (1999) Palladium(II)-catalyzed oxidative ring cleavage of tertcyclobutanols under oxygen atmosphere. J Am Chem Soc 121(11): 2645-2646. doi: 10. 1021/ja984259h.
41. Nishimura T, Uemura S (1999) Palladium-catalyzed arylation of tert-cyclobutanols with aryl bromide via C-C bond cleavage: new approach for the γ-arylated ketones. J Am Chem Soc 121 (47): 11010-11011. doi: 10. 1021/ja993023q.
42. Nishimura T, Matsumura S, Maeda Y, Uemura S (2002) Palladium-catalysed asymmetric arylation of tert-cyclobutanols via enantioselective C-C bond cleavage. Chem Commun 7 (1): 50-51. doi: 10. 1039/b107736h.
43. Matsumura S, Maeda Y, Nishimura T, Uemura S (2003) Palladium-catalyzed asymmetric arylation, vinylation, and allenylation of tert-cyclobutanols via enantioselective C-C bond cleavage. J Am Chem Soc 125(29): 8862-8869. doi: 10. 1021/ja035293l.
44. Seiser T, Cramer N (2008) Enantioselective C-C bond activation of allenyl cyclobutanes: access to cyclohexenones with quaternary stereogenic centers. Angew Chem Int Ed 47(48): 9294-9297. doi: 10. 1002/anie. 200804281.
45. Seiser T, Cramer N (2010) Rhodium(I)-catalyzed enantioselective activation of cyclobutanols: formation of cyclohexane derivatives with quaternary stereogenic centers. Chem-Eur J 16(11): 3383-3391. doi: 10. 1002/chem. 200903225.
46. Seiser T, Roth OA, Cramer N (2009) Enantioselective synthesis of indanols from tertcyclobutanols using a rhodium-catalyzed C-C/C-H activation sequence. Angew Chem Int Ed 48(34): 6320-6323. doi: 10. 1002/anie. 200903189.
47. Shigeno M, Yamamoto T, Murakami M (2009) Stereoselective restructuring of 3-arylcyclobutanols into 1-indanols by sequential breaking and formation of carbon-carbon bonds. Chem-Eur J 15(47): 12929-12931. doi: 10. 1002/chem. 200902593.
48. Seiser T, Cathomen G, Cramer N (2010) Enantioselective construction of indanones from cyclobutanols using a rhodium-catalyzed C-C/C-H/C-C bond activation process. Synlett 11: 1699-1703. doi: 10. 1055/s-0029-1219959.
49. Seiser T, Cramer N (2010) Rhodium(I)-catalyzed 1, 4-silicon shift of unactivated silanes from aryl to alkyl: enantioselective synthesis of indanol derivatives. Angew Chem Int Ed 49(52): 10163-10167. doi: 10. 1002/anie. 201005399.
50. Seiser T, Cramer N (2010) Rhodium-catalyzed C-C bond cleavage: construction of acyclic methyl substituted quaternary stereogenic centers. J Am Chem Soc 132(15): 5340-5341. doi: 10. 1021/ja101469t.
51. Ishida N, Sawano S, Murakami M (2012) Synthesis of 3, 3-disubstituted α-tetralones by rhodium-catalysed reaction of 1-(2-haloaryl)cyclobutanols. Chem Commun 48(14): 1973-1975. doi: 10. 1039/c2cc16907j.
52. Hayashi S, Hirano K, Yorimitsu H, Oshima K (2006) Palladium-catalyzed stereo-and regiospecific allylation of aryl halides with homoallyl alcohols via retro-allylation: selective generation and use of σ-allylpalladium. J Am Chem Soc 128(7): 2210-2211. doi: 10. 1021/ja058055u.
53. Shintani R, Takatsu K, Hayashi T (2008) Rhodium-catalyzed kinetic resolution of tertiary homoallyl alcohols via stereoselective carbon carbon bond cleavage. Org Lett 10(6): 1191-1193. doi: 10. 1021/ol800120p.
54. Waibel M, Cramer N (2010) Palladium-catalyzed arylative ring-opening reactions of norbornenols: entry to highly substituted cyclohexenes, quinolines, and tetrahydroquinolines. Angew Chem Int Ed 49(26): 4455-4458. doi: 10. 1002/anie. 201001752.
55. Waibel M, Cramer N (2011) Desymmetrizations of meso-tert-norbornenols by rhodium(I)-catalyzed enantioselective retro-allylations. Chem Commun 47(1): 346-348. doi: 10. 1039/c0cc01950j.
56. Terao Y, Wakui H, Nomoto M, Satoh T, Miura M, Nomura M (2003) Palladium-catalyzed arylation of α, α-disubstituted arylmethanols via cleavage of a C C or a C H bond to give biaryls. J Org Chem 68(13): 5236-5243. doi: 10. 1021/jo0344034.
57. Zhao P, Incarvito CD, Hartwig JF (2006) Direct observation of β-aryl eliminations from Rh(I) alkoxides. J Am Chem Soc 128(10): 3124-3125. doi: 10. 1021/ja058550q.
58. Nishimura T, Katoh T, Hayashi T (2007) Rhodium-catalyzed aryl transfer from trisubstituted aryl methanols to α, β-unsaturated carbonyl compounds. Angew Chem Int Ed 46(26): 4937-4939. doi: 10. 1002/anie. 200700902.
59. Nishimura T, Katoh T, Takatsu K, Shintani R, Hayashi T (2007) Rhodium-catalyzed asymmetric rearrangement of alkynyl alkenyl carbinols: synthetic equivalent to asymmetric conjugate alkynylation of enones. J Am Chem Soc 129(46): 14158-14159. doi: 10. 1021/ja076346s.
60. Nemoto H, Yoshida M, Fukumoto K (1997) Allenylcyclobutanol, a versatile initiator for the palladium-catalyzed cascade reaction: a novel route to bicyclo[5. 3. 0] and-[6. 3. 0] frameworks. J Org Chem 62(19): 6450-6451. doi: 10. 1021/jo9712310.
61. Trost BM, Yasukata T (2001) A catalytic asymmetric Wagner Meerwein shift. J Am Chem Soc 123(29): 7162-7163. doi: 10. 1021/ja010504c.
62. Trost BM, Xie J (2006) Palladium-catalyzed asymmetric ring expansion of allenylcyclobutanols: an asymmetric Wagner Meerwein shift. J Am Chem Soc 128(18): 6044-6045. doi: 10. 1021/ja0602501.
63. Trost BM, Xie J (2008) Palladium-catalyzed diastereo-and enantioselective Wagner Meerwein shift: control of absolute stereochemistry in the C C bond migration event. J Am Chem Soc 130(19): 6231-6242. doi: 10. 1021/ja7111299.
64. Kleinbeck F, Toste FD (2009) Gold(I)-catalyzed enantioselective ring expansion of allenylcyclopropanols. J Am Chem Soc 131(26): 9178-9179. doi: 10. 1021/ja904055z.
65. Wender PA, Gamber GG, Williams TJ (2005) Rhodium(I)-catalyzed [5+2], [6+2], and [5+2 +1] cycloadditions: new reactions for organic synthesis. In: Modern rhodium-catalyzed organic reactions. Wiley-VCH Verlag GmbH & Co. KGaA, pp 263-299. doi: 10. 1002/3527604693. ch13.
66. Ylijoki KEO, Stryker JM (2012) [5+2] Cycloaddition reactions in organic and natural product synthesis. Chem Rev 113(3): 2244-2266. doi: 10. 1021/cr300087g.
67. Wender PA, Haustedt LO, Lim J, Love JA, Williams TJ, Yoon J-Y (2006) Asymmetric catalysis of the [5+2] cycloaddition reaction of vinylcyclopropanes and π-systems. J Am Chem Soc 128(19): 6302-6303. doi: 10. 1021/ja058590u.
68. Shintani R, Nakatsu H, Takatsu K, Hayashi T (2009) Rhodium-catalyzed asymmetric [5+2] cycloaddition of alkyne-vinylcyclopropanes. Chem Eur J 15(35): 8692-8694. doi: 10. 1002/chem. 200901463.
69. Brandi A, Cicchi S, Cordero FM, Goti A (2003) Heterocycles from alkylidenecyclopropanes. Chem Rev 103(4): 1213-1270. doi: 10. 1021/cr010005u.
70. Rubin M, Rubina M, Gevorgyan V (2007) Transition metal chemistry of cyclopropenes and cyclopropanes. Chem Rev 107(7): 3117-3179. doi: 10. 1021/cr050988l.
71. Masarwa A, Marek I (2010) Selectivity in metal-catalyzed carbon-carbon bond cleavage of alkylidenecyclopropanes. Chem Eur J 16(32): 9712-9721. doi: 10. 1002/chem. 201001246.
72. Suginome M, Matsuda T, Ito Y (2000) Palladium-and platinum-catalyzed silaboration of methylenecyclopropanes through selective proximal or distal C C bond cleavage. J Am Chem Soc 122(44): 11015-11016. doi: 10. 1021/ja002885k.
73. Ohmura T, Taniguchi H, Kondo Y, Suginome M (2007) Palladium-catalyzed asymmetric silaborative C C cleavage of meso-methylenecyclopropanes. J Am Chem Soc 129(12): 3518-3519. doi: 10. 1021/ja0703170.
74. Akai Y, Yamamoto T, Nagata Y, Ohmura T, Suginome M (2012) Enhanced catalyst activity and enantioselectivity with chirality-switchable polymer ligand PQXphos in Pd-catalyzed asymmetric silaborative cleavage of meso-methylenecyclopropanes. J Am Chem Soc 134(27): 11092-11095. doi: 10. 1021/ja303506k.
75. Gulıás M, Durán J, López F, Castedo L, Mascarenãs JL (2007) Palladium-catalyzed [4+3] intramolecular cycloaddition of alkylidenecyclopropanes and dienes. J Am Chem Soc 129(36): 11026-11027. doi: 10. 1021/ja0756467.
76. Mazumder S, Shang D, Negru DE, Baik M-H, Evans PA (2012) Stereoselective rhodiumcatalyzed [3+2+1] carbocyclization of alkenylidenecyclopropanes with carbon monoxide: theoretical evidence for a trimethylenemethane metallacycle intermediate. J Am Chem Soc 134(51): 20569-20572. doi: 10. 1021/ja305467x.
77. McKinney RJ (1992) The applications and chemistry of catalysis by soluble transition metal complexes. In: Homogeneous catalysis. Wiley, New York, pp 42-50.
78. Tolman CA, Seidel WC, Druliner JD, Domaille PJ (1984) Catalytic hydrocyanation of olefins by nickel(0) phosphite complexes-effects of Lewis acids. Organometallics 3(1): 33-38. doi: 10. 1021/om00079a008.
79. Nakao Y, Oda S, Hiyama T (2004) Nickel-catalyzed arylcyanation of alkynes. J Am Chem Soc 126(43): 13904-13905. doi: 10. 1021/ja0448723.
80. Nakao Y, Yukawa T, Hirata Y, Oda S, Satoh J, Hiyama T (2006) Allylcyanation of alkynes: regio-and stereoselective access to functionalized di-or trisubstituted acrylonitriles. J Am Chem Soc 128(22): 7116-7117. doi: 10. 1021/ja060519g.
81. Nakao Y, Yada A, Ebata S, Hiyama T (2007) A dramatic effect of Lewis-acid catalysts on nickel-catalyzed carbocyanation of alkynes. J Am Chem Soc 129(9): 2428-2429. doi: 10. 1021/ja067364x.
82. Nakao Y, Hirata Y, Tanaka M, Hiyama T (2008) Nickel/BPh3-catalyzed alkynylcyanation of alkynes and 1, 2-dienes: an efficient route to highly functionalized conjugated enynes. Angew Chem Int Ed 47(2): 385-387. doi: 10. 1002/anie. 200704095.
83. Nakao Y (2012) Nickel/Lewis acid-catalyzed carbocyanation of unsaturated compounds. Bull Chem Soc Jpn 85(7): 731-745.
84. Watson MP, Jacobsen EN (2008) Asymmetric intramolecular arylcyanation of unactivated olefins via C CN bond activation. J Am Chem Soc 130(38): 12594-12595. doi: 10. 1021/ja805094j.
85. Nakao Y, Ebata S, Yada A, Hiyama T, Ikawa M, Ogoshi S (2008) Intramolecular arylcyanation of alkenes catalyzed by nickel/AlMe2Cl. J Am Chem Soc 130 (39): 12874-12875. doi: 10. 1021/ja805088r.
86. Nájera C, Sansano JM (2009) Asymmetric intramolecular carbocyanation of alkenes by C-C bond activation. Angew Chem Int Ed 48(14): 2452-2456. doi: 10. 1002/anie. 200805601.
87. Hsieh J-C, Ebata S, Nakao Y, Hiyama T (2010) Asymmetric synthesis of indolines bearing a benzylic quaternary stereocenter through intramolecular arylcyanation of alkenes. Synlett 2010(11): 1709-1711. doi: 10. 1055/s-0029-1219964.
88. Murahashi S, Naota T, Nakajima N (1986) Palladium-catalyzed decarbonylation of acyl cyanides. J Org Chem 51(6): 898-901. doi: 10. 1021/jo00356a029.
89. Yasui Y, Kamisaki H, Takemoto Y (2008) Enantioselective synthesis of 3, 3-disubstituted oxindoles through Pd-catalyzed cyanoamidation. Org Lett 10(15): 3303-3306. doi: 10. 1021/ol801168j.
90. Yasui Y, Kamisaki H, Ishida T, Takemoto Y (2010) Synthesis of 3, 3-disubstituted oxindoles through Pd-catalyzed intramolecular cyanoamidation. Tetrahedron 66(11): 1980-1989, http://dx. doi. org/10. 1016/j. tet. 2010. 01. 073.