RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2005(13): 2091-2115
DOI: 10.1055/s-2005-872084
DOI: 10.1055/s-2005-872084
REVIEW
© Georg Thieme Verlag Stuttgart · New York
Boron-Substituted Building Blocks in Diels-Alder and Other Cycloaddition Reactions
Weitere Informationen
Received
4 March 2005
Publikationsdatum:
20. Juli 2005 (online)
Publikationsverlauf
Publikationsdatum:
20. Juli 2005 (online)
Abstract
Boron-containing building blocks are among the most prominent starting materials in several transformations based on their wide range of synthetic applications. Over the last decade various cycloaddition reactions were reported where boron-containing 1,3-dienes or boron-containing dienophiles were used. Combined with the broad follow-up chemistry, target-oriented as well as diversity-oriented syntheses could be established.
-
1 Introduction
-
2 Boron-Functionalised 1,3-Dienes
-
2.1 Boron in Position 1
-
2.2 Boron in Position 2
-
3 Boron-Functionalised Dienophiles
-
3.1 Alkenyl Boron Reagents
-
3.2 Alkynyl Boron Reagents
-
4 Boron Reagents in 1,3-Dipolar Cycloaddition
-
5 Miscellaneous
-
6 Outlook
Key words
boron - cycloaddition - cyclotrimerisation - Diels-Alder reaction - 1,3-dipole
-
1a
Albrecht K.Kaufmann D. In Science of Synthesis (Houben-Weyl), Vol. 6 Thieme; New York: 2004. p.697 -
1b
Vaultier M.Alcaraz G. In Science of Synthesis (Houben-Weyl), Vol. 6 Thieme; New York: 2004. p.721 -
1c
Miyaura N. Top. Curr. Chem. 2002, 219: 11 -
1d
Vaultier M.Lorvelec G.Plunian W.Paulus O.Bouju P.Mortier J. Royal Soc. Chem. 2000, 253: 464 -
1e
Matteson DS. In Stereodirected Synthesis with Organoboranes Springer; Berlin: 1995. -
1f
Miyaura N.Suzuki A. Chem. Rev. 1995, 95: 2457 -
1g
Matteson DS. Tetrahedron 1989, 45: 1859 - 2
Vaultier M.Truchet F.Carboni B.Hoffmann RW.Denne I. Tetrahedron Lett. 1987, 28: 4169 - 3
Mazal C.Vaultier M. Tetrahedron Lett. 1994, 35: 3089 - 4
Mikhailov BM.Cherkasova KL. Zh. Obshch. Khim. 1972, 42: 138 - 5
Mikhailov BM.Cherkasova KL. Zh. Obshch. Khim. 1972, 42: 1744 - 6
Renard P.-Y.Six Y.Lallemand J.-Y. Tetrahedron Lett. 1997, 38: 6589 - 7
Renard P.-Y.Lallemand J.-Y. Tetrahedron: Asymmetry 1996, 7: 2523 - 8
Garnier L.Plunian B.Mortier J.Vaultier M. Tetrahedron Lett. 1996, 37: 6699 - 9
Gao X.Hall DG. Tetrahedron Lett. 2003, 44: 2231 - 10
Wang X. J. Chem. Soc., Chem. Commun. 1991, 1515 - 11
Zhang A.Kan Y.Jiang B. Tetrahedron 2001, 57: 2305 - 12
Mortier J.Vaultier M.Plunian B.Toupet L. Heterocycles 1999, 50: 703 - 13
Renard P.-Y.Lallemand J.-Y. Bull. Soc. Chim. Fr. 1996, 133: 143 - 14
Ohanessian G.Six Y.Lallemand J.-Y. Bull. Soc. Chim. Fr. 1996, 133: 1143 - 15
Six Y.Lallemand J.-Y. Tetrahedron Lett. 1999, 40: 1295 - 16
Lallemand J.-Y.Six Y.Ricard L. Eur. J. Org. Chem. 2002, 503 - 17
Jehanno E.Vaultier M. Tetrahedron Lett. 1995, 36: 4439 - 18
Rasset-Deloge C.Martinez-Fresneda P.Vaultier M. Bull. Soc. Chim. Fr. 1992, 129: 285 - 19
Deligny M.Carreaux F.Carboni B.Toupet L.Dujardin G. Chem. Commun. 2003, 276 - 20
Deligny M.Carreaux F.Toupet L.Carboni B. Adv. Synth. Catal. 2003, 345: 1215 - 21
Gao X.Hall DG. J. Am. Chem. Soc. 2003, 125: 9308 - 22
Gao X.Hall DG. J. Am. Chem. Soc. 2005, 127: 1628 - 23
Stierle DB.Stierle AA. Experientia 1992, 48: 1165 - 24
Tailor J.Hall DG. Org. Lett. 2000, 2: 3715 - 25
Touré BB.Hoveyda HR.Tailor J.Ulaczyk-Lesanko A.Hall DG. Chem.-Eur. J. 2003, 9: 466 - 26
Touré BB.Hall DG. J. Org. Chem. 2004, 69: 8429 - 27
Touré BB.Hall DG. Angew. Chem. Int. Ed. 2004, 43: 2001 ; Angew. Chem. 2004, 116, 2035 - 28
Guennouini N.Rasset-Deloge C.Carboni B.Vaultier M. Synlett 1992, 581 - 29
Kamabuchi A.Miyaura N.Suzuki A. Tetrahedron Lett. 1993, 34: 4827 - 30
Carreaux F.Possémé F.Carboni B.Arrieta A.Lecea B.Cossío FP. J. Org. Chem. 2002, 67: 9153 - 31
Shimizu M.Kurahashi T.Hiyama T. Synlett 2001, 1006 - 32
Kurahashi T.Hata T.Masai H.Kitagawa H.Shimizu M.Hiyama T. Tetrahedron 2002, 58: 6381 - 33
Waas JR.Sidduri A.Knochel P. Tetrahedron Lett. 1992, 33: 3717 - 34
Renaud J.Graf C.-D.Oberer L. Angew. Chem. Int. Ed. 2000, 39: 3101 ; Angew. Chem. 2000, 112, 3231 - 35
Wrackmeyer B.Milius W.Bhatti MH.Ali S. J. Organomet. Chem. 2003, 665: 196 - 36
Kaufmann DE. Chem. Ber. 1987, 120: 901 - 37
Kaufmann DE.Schacht W. Chem. Ber. 1987, 120: 1331 - 38
Eisch JJ.Kotowicz BW. Eur. J. Inorg. Chem. 1998, 761 - 39
Matteson DS.Wasserbillig JO. J. Org. Chem. 1963, 28: 366 - 40
Matteson DS.Talbot ML. J. Am. Chem. Soc. 1967, 89: 1123 - 41
Woods WG.Bengelsdorf IS. J. Org. Chem. 1966, 31: 2769 - 42
Evans DA.Scott WL.Truesdale LK. Tetrahedron Lett. 1972, 2: 121 - 43
Bonk JD.Avery MA. Tetrahedron: Asymmetry 1997, 8: 1149 - 44
Singleton DA.Martinez JP. J. Am. Chem. Soc. 1990, 112: 7423 - 45
Singleton DA.Martinez JP.Ndip GM. J. Org. Chem. 1992, 57: 5768 - 46
Singleton DA.Martinez JP.Watson JV.Ndip GM. Tetrahedron 1992, 48: 5831 - 47
Singleton DA.Martinez JP.Watson JV. Tetrahedron Lett. 1992, 33: 1017 - 48
Singleton DA.Martinez JP. Tetrahedron Lett. 1991, 32: 7365 - 49
Coindard G.Braun J. Bull. Soc. Chim. Fr. 1972, 817 - 50
Singleton DA.Kim K.Martinez JP. Tetrahedron Lett. 1993, 34: 3071 - 51
Jego J.-M.Carboni B.Youssofi A.Vaultier M. Synlett 1993, 595 - 52
Noiret N.Youssofi A.Carboni B.Vaultier M. J. Chem. Soc., Chem. Commun. 1992, 1105 - 53
Lee Y.-K.Singleton DA. J. Org. Chem. 1997, 62: 2255 - 54
Singleton DA. J. Am. Chem. Soc. 1992, 114: 6563 - 55
Silva MA.Pellegrinet SC.Goodman JM. Arkivoc 2003, x: 556 - 56
Pellegrinet SC.Silva MA.Goodman JM. J. Am. Chem. Soc. 2001, 123: 8832 - 57
Pellegrinet SC.Silva MA.Goodman JM. J. Comput. Aided Mol. Des. 2004, 18: 209 - 58
Singleton DA.Redman AM. Tetrahedron Lett. 1994, 35: 509 - 59
Singleton DA.Leung S.-W. J. Organomet. Chem. 1997, 544: 157 - 60
Martinez-Fresneda P.Vaultier M. Tetrahedron Lett. 1989, 30: 2929 - 61
Rasset C.Vaultier M. Tetrahedron 1994, 50: 3397 - 62
Lorvelec G.Vaultier M. Tetrahedron Lett. 1998, 39: 5185 - 63
Singleton DA.Lee Y.-K. Tetrahedron Lett. 1995, 36: 3473 - 64
Batey RA.Lin D.Wong A.Hayhoe CLS. Tetrahedron Lett. 1997, 38: 3699 - 65
Batey RA.Thadani AN.Lough AJ. Chem. Commun. 1999, 475 - 66
Batey RA.Thadani AN.Lough AJ. J. Am. Chem. Soc. 1999, 121: 450 - 67
Narasaka K.Yamamoto I. Tetrahedron 1992, 48: 5743 - 68
Yamamoto I.Narasaka K. Bull. Chem. Soc. Jpn. 1994, 67: 3327 - 69
Blanchard C.Framery E.Vaultier M. Synthesis 1996, 45 - 70
Brown HC.Bhat NG.Srebnik M. Tetrahedron Lett. 1988, 29: 2631 - 71 For a review on the chemistry of alkynyl boronates, see:
Negishi E. In Comprehensive Organometallic Chemistry Vol. 7:Wilkinson G.Stone FGA.Abel EW. Pergamon; Oxford: 1983. p.337 - 72
Matteson DS.Peacock K. J. Am. Chem. Soc. 1960, 82: 5759 - 73
Matteson DS. J. Org. Chem. 1962, 27: 4293 - 74
Seitz G.Haenel F. Arch. Pharm. 1994, 327: 673 - 75
Leung S.-W.Singleton DA. J. Org. Chem. 1997, 62: 1955 - 76
Singleton DA.Leung S.-W. J. Org. Chem. 1992, 57: 4796 - 78
Silva MA.Pellegrinet SC.Goodman JM. J. Org. Chem. 2003, 68: 4059 - 79
Silva MA.Pellegrinet SC.Goodman JM. J. Org. Chem. 2002, 67: 8203 - 80
Silva MA.Goodman JM. Tetrahedron Lett. 2003, 44: 8233 -
81a
Davies MW.Johnson CN.Harrity JPA. Chem. Commun. 1999, 2107 -
81b For a recent review, see:
Dötz KH.Tomuschat P. Chem. Soc. Rev. 1999, 28: 187 - 82
Yamashita A.Tay A. Tetrahedron Lett. 1986, 27: 3471 - 83
Davies MW.Johnson CN.Harrity JPA. J. Org. Chem. 2001, 66: 3525 -
84a
Vollhardt KPC.Eichberg MJ. In Strategies and Tactics in Organic Synthesis Elsevier; London: 2004. p.365 -
84b
Varela JA.Saa C. Chem. Rev. 2003, 103: 3787 -
84c
Saito S.Yamamoto Y. Chem. Rev. 2000, 100: 2901 -
84d
Vollhardt KPC. Lect. Heterocycl. Chem. 1987, 9: 59 - 85
Gu Y.Pritzkow H.Siebert W. Eur. J. Inorg. Chem. 2001, 373 - 86
Goswami A.Maier C.-J.Pritzkow H.Siebert W. Eur. J. Org. Chem. 2004, 2635 - 87
Gandon V.Leca D.Aechtner T.Vollhardt KPC.Malacria M.Aubert C. Org. Lett. 2004, 6: 3405 - 88
Ester C.Maderna A.Pritzkow H.Siebert W. Eur. J. Inorg. Chem. 2000, 1177 - 89
Yamamoto Y.Ishii J.-i.Nishiyama H.Itoh K. J. Am. Chem. Soc. 2004, 126: 3712 - 90
Hilt G.Smolko KI. Angew. Chem. 2003, 115: 2901 ; Angew. Chem. Int. Ed. 2003, 42, 2795 - 91
Hilt G.Hess W.Schmidt F. Eur. J. Org. Chem. 2005, in press - 92
Hilt G.Lüers S.Smolko KI. Org. Lett. 2005, 7: 251 - 93
Jazouli M.Carboni B.Carrié R.Soufiaoui M.Toupet L. Heteroat. Chem. 1994, 5: 513 - 94
Wallace RH.Zong KK. Tetrahedron Lett. 1992, 33: 6941 - 95
Bast K.Christl M.Huisgen R.Mack W.Sustmann R. Chem. Ber. 1973, 106: 3258 - 96
Mukaiyama T.Hoshimo T. J. Am. Chem. Soc. 1960, 82: 5339 - 97
Jazouli M.Baba S.Carboni B.Carrié R.Soufiaoui M. J. Organomet. Chem. 1995, 498: 229 - 98
Wallace RH.Liu J. Tetrahedron Lett. 1994, 35: 7493 - 99
Grünanger P.Vita-Finzi P. In Isoxazoles Vol. 49, Part 1: Wiley; New York: 1991. p.417 - 100
Wallace RH.Liu J.Zong KK.Eddings A. Tetrahedron Lett. 1997, 38: 6791 - 101
Lui J.Eddings A.Wallace RH. Tetrahedron Lett. 1997, 38: 6795 - 102
Zhang A.Kan Y.Zhao G.-L.Jiang B. Tetrahedron 2000, 56: 965 - 103
Wallace RH.Zong KK. J. Organomet. Chem. 1999, 581: 87 - 104
Davies CD.Marsden SP.Stokes ESE. Tetrahedron Lett. 1998, 39: 8513 - 105
Davies CD.Marsden SP.Stokes ESE. Tetrahedron Lett. 2000, 41: 4229 - 106
Jiang B.Zhang A.Ying K. Chin. J. Chem. 1999, 17: 293 - 107
Bianchi G.Cogoli A.Grünanger P. J. Organomet. Chem. 1966, 6: 598 - 108
Davies MW.Wybrow RAJ.Johnson CN.Harrity JPA. Chem. Commun. 2001, 1558 - 109
Moore JE.Goodenough KM.Spinks D.Harrity JPA. Synlett 2002, 2071 - 110
Carboni B.Ollivault M.Le Bouguenec F.Carrié R.Jazouli M. Tetrahedron Lett. 1997, 38: 6665 - 111
Belfaitah A.Isly M.Carboni B. Tetrahedron Lett. 2004, 45: 1969 - 112
Rastelli A.Gandolfi R.Sarzi-Amade M.Carboni B. J. Org. Chem. 2001, 66: 2449 - 113
Sáez J.Arnó M.Domingo LR. Tetrahedron 2003, 59: 9167 - 114
Micalizio GC.Schreiber SL. Angew. Chem. Int. Ed. 2002, 41: 152 ; Angew. Chem. 2002, 114, 160 - 115
Micalizio GC.Schreiber SL. Angew. Chem. Int. Ed. 2002, 41: 3272 ; Angew. Chem. 2002, 114, 3406 - 116
Pietruska J.Witt A. J. Chem. Soc., Perkin Trans. 1 2000, 4293 - 117
Markó IE.Kumamoto T.Giard T. Adv. Synth. Catal. 2002, 344: 1063 - 118
Markó IE.Giard T.Sumida S.Gies A.-E. Tetrahedron Lett. 2002, 43: 2317 - 119
Matteson DS.Schaumberg GD. J. Org. Chem. 1966, 31: 726 - 120
Bubnov YN.Nesmeyanova OA.Rudashevkaya TY.Mikhailov BM.Kazansky BA. Tetrahedron Lett. 1971, 24: 2153 - 121
Little RD.Bode H.Stone KJ.Wallquist O.Dannecker R. J. Org. Chem. 1985, 50: 2401 - 122
Fontani P.Carboni B.Vaultier M.Carrié R. Tetrahedron Lett. 1989, 30: 4815 - 123
Fontani P.Carboni B.Vaultier M.Maas G. Synthesis 1991, 605 - 124
Imai T.Mineta H.Nishida S. J. Org. Chem. 1990, 55: 4986 -
125a
Luithle JEA.Pietruszka J. Liebigs Ann./Recl. 1997, 2297 -
125b
Pietruszka J.Widenmeyer M. Synlett 1997, 977 -
125c
Luithle JEA.Pietruszka J.Witt A. Chem. Commun. 1998, 2651 -
125d
Luithle JEA.Pietruszka J. J. Org. Chem. 1999, 64: 8287 -
125e
Luithle JEA.Pietruszka J. J. Org. Chem. 2000, 65: 9194 -
126a
Wang X.-Z.Deng M.-Z. J. Chem. Soc., Perkin Trans. 1 1996, 2663 -
126b
Zhou S.-M.Yan Y.-L.Deng M.-Z. Synlett 1998, 198 -
126c
Zhou S.-M.Deng M.-Z.Xia L.-J.Tang M.-H. Angew. Chem. Int. Ed. 1998, 37: 2845 ; Angew. Chem. 1998, 110, 3061 - 127
Hildebrand JP.Marsden SP. Synlett 1996, 893 - 128
Charette AB.Pereira De Freitas-Gil R. Tetrahedron Lett. 1997, 38: 2809 - 129
Desurmont G.Klein R.Uhlenbrock S.Laloë E.Deloux L.Giolando DM.Kim YW.Pereira S.Srebnik M. Organometallics 1996, 15: 3323 - 130
Desurmont G.Dalton S.Giolando DM.Srebnik M. J. Org. Chem. 1997, 62: 8907 - 131
Hollis WG.Lappenbusch WC.Everberg KA.Woleben CM. Tetrahedron Lett. 1993, 34: 7517 - 132
Thormeier S.Carboni B.Kaufmann DE. J. Organomet. Chem. 2002, 657: 136
References
Early calculations on a RHF/3-21G level were consistent with the observed chemical behavior; compare ref. 76.