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Directed Metallation pp 169–192Cite as

Directed Mizoroki–Heck Reactions

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Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 24))

Abstract

The Mizoroki–Heck reaction is one of the key C–C bond-forming processes in organic synthesis. A prominent variant, which has found broadest application in targeted complex molecule synthesis, is the asymmetric intramolecular Mizoroki–Heck reaction. This methodology has outshone another powerful facet of Mizoroki–Heck chemistry, which has been prospering in recent years, namely directed Mizoroki–Heck reactions. Initially designed to achieve high regiocontrol in intermolecular reactions, this technique has recently been extended to highly diastereoselective and even enantioselective substrate-directed inter- as well as intramolecular Mizoroki–Heck reactions. This summary delineates the evolution of this chemistry from regio- to diastereo- and finally, enantioselective transformations.

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References

  1. Oestreich M (2005) Eur J Org Chem 783

    Google Scholar 

  2. de Meijere A, Diederich F (2004) Metal-Catalyzed Cross-Coupling Reactions. Wiley, Weinheim

    Book  Google Scholar 

  3. Beller M, Bolm C (2004) Transition Metals for Organic Synthesis—Building Blocks and Fine Chemicals. Wiley, Weinheim

    Google Scholar 

  4. Negishi E, de Meijere A (2002) Handbook of Organopalladium Chemistry for Organic Synthesis. Wiley, New York

    Google Scholar 

  5. Mizoroki T, Mori K, Ozaki A (1971) Bull Chem Soc Jpn 44:581

    Article  CAS  Google Scholar 

  6. Heck RF, Nolley JP Jr (1972) J Org Chem 37:2320

    Article  CAS  Google Scholar 

  7. Larhed M, Hallberg A (2002) Scope, Mechanism, and Other Fundamental Aspects of the Intermolecular Heck Reaction. In: Negishi E, de Meijere A (eds) Handbook of Organopalladium Chemistry for Organic Synthesis. Wiley, New York, p 1133

    Chapter  Google Scholar 

  8. Beletskaya IP, Cheprakov AV (2000) Chem Rev 100:3009

    Article  CAS  Google Scholar 

  9. Link JT (2002) The Intramolecular Heck Reaction. In: Overman LE (ed) Organic Reactions, Vol. 60. Wiley, New York, p 157

    Google Scholar 

  10. Bräse S, de Meijere A (2002) Synthesis of Carbocycles. In: Negishi E, de Meijere A (eds) Handbook of Organopalladium Chemistry for Organic Synthesis. Wiley, New York, p 1223

    Chapter  Google Scholar 

  11. Sato Y, Sodeoka M, Shibasaki M (1989) J Org Chem 54:4738

    Article  CAS  Google Scholar 

  12. Carpenter NE, Kucera DJ, Overman LE (1989) J Org Chem 54:5846

    Article  CAS  Google Scholar 

  13. Guiry PJ, Kiely D (2004) Curr Org Chem 8:781

    Article  CAS  Google Scholar 

  14. Shibasaki M, Miyazaki F (2002) Asymmetric Heck Reactions. In: Negishi E, de Meijere A (eds) Handbook of Organopalladium Chemistry for Organic Synthesis. Wiley, New York, p 1283

    Chapter  Google Scholar 

  15. Donde Y, Overman LE (2000) Asymmetric Intramolecular Heck Reactions. In: Ojima I (ed) Catalytic Asymmetric Synthesis. Wiley, New York, p 675

    Google Scholar 

  16. Shibasaki M, Vogl EM (1999) Heck Reaction. In: Jacobsen EN, Pfaltz A, Yamamoto H (eds) Comprehensive Asymmetric Catalysis I–III. Springer, Berlin Heidelberg New York, p 457

    Google Scholar 

  17. Dounay AB, Overman LE (2003) Chem Rev 103:2945

    Article  CAS  Google Scholar 

  18. Link JT, Overman LE (1998) Intramolecular Heck Reactions in Natural Product Chemistry. In: Diederich F, Stang PJ (eds) Metal-Catalyzed Cross-Coupling Reactions. Wiley, New York, p 231

    Google Scholar 

  19. Ozawa F, Kubo A, Hayashi T (1991) J Am Chem Soc 113:1417

    Article  CAS  Google Scholar 

  20. Loiseleur O, Hayashi M, Keenan M, Schmess N, Pfaltz A (1999) J Organomet Chem 576:16

    Article  CAS  Google Scholar 

  21. Jutand A (2003) Eur J Inorg Chem 2017

    Google Scholar 

  22. Amatore C, Jutand A (1999) J Organomet Chem 576:254

    Article  CAS  Google Scholar 

  23. Andersson CM, Larsson J, Hallberg A (1990) J Org Chem 55:5757

    Article  CAS  Google Scholar 

  24. Larhed M, Andersson CM, Hallberg A (1993) Acta Chem Scand 47:212

    Article  CAS  Google Scholar 

  25. Larhed M, Andersson CM, Hallberg A (1994) Tetrahedron 50:285

    Article  CAS  Google Scholar 

  26. Stadler A, von Schenck H, Vallin KSA, Larhed M, Hallberg A (2004) Adv Synth Catal 346:1773

    Article  CAS  Google Scholar 

  27. Hoveyda AH, Evans DA, Fu GC (1993) Chem Rev 93:1307

    Article  CAS  Google Scholar 

  28. Breit B (2000) Chem Eur J 6:1519

    Article  CAS  Google Scholar 

  29. Reetz MT (1984) Angew Chem 96:542

    Article  CAS  Google Scholar 

  30. Reetz MT (1984) Angew Chem Int Ed Engl 23:556

    Article  Google Scholar 

  31. Beak P, Meyers AI (1986) Acc Chem Res 19:356

    Article  CAS  Google Scholar 

  32. Whisler MC, MacNeil S, Snieckus V, Beak P (2004) Angew Chem 116:2256

    Article  Google Scholar 

  33. Whisler MC, MacNeil S, Snieckus V, Beak P (2004) Angew Chem Int Ed 43:2206

    Article  CAS  Google Scholar 

  34. Jeffery T (1996) Recent Improvements and Developments in Heck-type Reactions and their Potential in Organic Synthesis. In: Liebeskind LS (ed) Advances in Metal-Organic Chemistry. JAI Press, Greenwich, p 153

    Google Scholar 

  35. Deeth RJ, Smith A, Brown JM (2004) J Am Chem Soc 126:7144

    Article  CAS  Google Scholar 

  36. McCrindle R, Ferguson G, Khan MA, McAlees AJ, Ruhl BL (1981) Dalton Trans, p 986

    Google Scholar 

  37. Kasahara A, Izumi T, Takeda T, Imamura H (1974) Bull Soc Chem Jpn 47:183

    Article  CAS  Google Scholar 

  38. Cross RJ (1989) Adv Inorg Chem 34:219

    Article  CAS  Google Scholar 

  39. Thorn DL, Hoffmann R (1978) J Am Chem Soc 100:2079

    Article  CAS  Google Scholar 

  40. Samsel EG, Norton JR (1984) J Am Chem Soc 106:5505

    Article  CAS  Google Scholar 

  41. Nilsson P, Larhed M, Hallberg A (2001) J Am Chem Soc 123:8217

    Article  CAS  Google Scholar 

  42. Itami K, Yoshida J (2006) Synlett, p 157

    Google Scholar 

  43. Itami K, Yoshida J (2006) Bull Soc Chem Jpn 79:811

    Article  CAS  Google Scholar 

  44. Itami K, Yoshida J (2006) Chem Eur J 12:3966

    Article  CAS  Google Scholar 

  45. Itami K, Mitsudo K, Kamei T, Koike T, Nokami T, Yoshida J (2000) J Am Chem Soc 122:12013

    Article  CAS  Google Scholar 

  46. Itami K, Nokami T, Ishimura Y, Mitsudo K, Kamei T, Yoshida J (2001) J Am Chem Soc 123:11577

    Article  CAS  Google Scholar 

  47. Itami K, Mineno M, Muraoka N, Yoshida J (2004) J Am Chem Soc 126:11778

    Article  CAS  Google Scholar 

  48. Itami K, Nokami T, Yoshida J (2001) J Am Chem Soc 123:5600

    Article  CAS  Google Scholar 

  49. Alonso I, Carretero JC (2001) J Org Chem 66:4453

    Article  CAS  Google Scholar 

  50. Kao LC, Stakem FG, Patel BA, Heck RF (1982) J Org Chem 47:1267

    Article  CAS  Google Scholar 

  51. Bernocchi E, Cacchi S, Ciattini PG, Morera E, Ortar G (1992) Tetrahedron Lett 33:3073

    Article  CAS  Google Scholar 

  52. Kang SK, Jung KY, Park CH, Namkoong EY, Kim TH (1995) Tetrahedron Lett 36:6287

    Article  CAS  Google Scholar 

  53. Ndungu JM, Larson KK, Sarpong R (2005) Org Lett 7:5845

    Article  CAS  Google Scholar 

  54. Kondolff I, Doucet H, Santelli M (2006) Eur J Org Chem 765

    Google Scholar 

  55. Ono K, Fugami K, Tanaka S, Tamaru Y (1994) Tetrahedron Lett 35:4133

    Article  CAS  Google Scholar 

  56. Olofsson K, Sahlin H, Larhed M, Hallberg A (2001) J Org Chem 66:544

    Article  CAS  Google Scholar 

  57. Oestreich M, Dennison PR, Kodanko JJ, Overman LE (2001) Angew Chem 113:1485

    Article  Google Scholar 

  58. Oestreich M, Dennison PR, Kodanko JJ, Overman LE (2001) Angew Chem Int Ed 40:1439

    Article  CAS  Google Scholar 

  59. Burke BJ, Overman LE (2004) J Am Chem Soc 126:16820

    Article  CAS  Google Scholar 

  60. Badone D, Guzzi U (1993) Tetrahedron Lett 34:3603

    Article  CAS  Google Scholar 

  61. Buezo ND, Alonso I, Carretero JC (1998) J Am Chem Soc 120:7129

    Article  Google Scholar 

  62. de la Rosa JC, Díaz N, Carretero JC (2000) Tetrahedron Lett 41:4107

    Article  Google Scholar 

  63. Buezo ND, de la Rosa JC, Priego J, Alonso I, Carretero JC (2001) Chem Eur J 7:3890

    Article  CAS  Google Scholar 

  64. Nilsson P, Larhed M, Hallberg A (2003) J Am Chem Soc 125:3430

    Article  CAS  Google Scholar 

  65. Buezo ND, Mancheño OG, Carretero JC (2000) Org Lett 2:1451

    Article  CAS  Google Scholar 

  66. Overman LE, Watson DA (2006) J Org Chem 71:2600

    Article  CAS  Google Scholar 

  67. Cabri W, Candiani I (1995) Acc Chem Res 28:2

    Article  CAS  Google Scholar 

  68. Earley WG, Oh T, Overman LE (1988) Tetrahedron Lett 29:3785

    Article  CAS  Google Scholar 

  69. Madin A, Overman LE (1992) Tetrahedron Lett 33:4859

    Article  CAS  Google Scholar 

  70. Oestreich M, Sempere-Culler F, Machotta AB (2005) Angew Chem 117:152

    Article  Google Scholar 

  71. Oestreich M, Sempere-Culler F, Machotta AB (2005) Angew Chem Int Ed 44:149

    Article  CAS  Google Scholar 

  72. Oestreich M, Sempere-Culler F, Machotta AB (2006) Synlett, p 2965

    Google Scholar 

  73. Ashimori A, Bachand B, Calter MA, Govek SP, Overman LE, Poon DJ (1998) J Am Chem Soc 120:6488

    Article  CAS  Google Scholar 

Download references

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Authors and Affiliations

  1. Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149, Münster, Germany

    Martin Oestreich

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  1. Martin Oestreich
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Correspondence to Martin Oestreich .

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Naoto Chatani

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© 2007 Springer-Verlag Berlin Heidelberg

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Oestreich, M. (2007). Directed Mizoroki–Heck Reactions. In: Chatani, N. (eds) Directed Metallation. Topics in Organometallic Chemistry, vol 24. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3418_2007_063

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