Subscribe to RSS
DOI: 10.1055/s-2006-950379
Tandem and Domino Catalytic Strategies for Enantioselective Synthesis
Publication History
Publication Date:
12 December 2006 (online)
Abstract
Catalytic asymmetric methodologies provide versatile routes to many complex molecules through expedient and often elegant processes. This review summarises the work on the development and application of tandem and domino catalysed reactions within enantioselective organic synthesis.
-
1 Introduction
-
2 Transition-Metal-Catalysed Processes
-
2.1 Processes Involving Michael Additions
-
2.2 Hydroformylations
-
2.3 Heck Reactions
-
2.4 Allylic Substitutions
-
2.5 Processes Involving Pericyclic Reactions
-
2.6 Hydrogenations
-
2.7 Aldol Reactions
-
2.8 Metathesis Reactions
-
2.9 Processes Involving Epoxide Formation
-
2.10 Miscellaneous Transition-Metal-Catalysed Processes
-
3 Chiral Organocatalytic Reactions
-
3.1 Processes Involving Michael Additions
-
3.2 Aldol Reactions
-
3.3 Mannich Reactions
-
3.4 Processes Involving Pericyclic Reactions
-
3.5 Miscellaneous Organocatalytic Processes
-
4 Conclusions
Key words
asymmetric catalysis - tandem reactions - domino reactions - multicomponent reactions - natural products
-
1a
Pellissier H. Tetrahedron 2006, 62: 2143 -
1b
Pellissier H. Tetrahedron 2006, 62: 1619 -
1c
Guo HC.Ma JA. Angew. Chem. Int. Ed. 2006, 45: 354 -
1d
Wasilke JC.Obrey SJ.Baker RT.Bazan GC. Chem. Rev. 2005, 105: 1001 -
1e
Ajamian A.Gleason JL. Angew. Chem. Int. Ed. 2004, 43: 3754 -
1f
Poli G.Giambastiani G.Heumann A. Tetrahedron 2000, 56: 5959 -
1g
Grigg R.Sridharan V. J. Organomet. Chem. 1999, 576: 65 -
1h
Mehta G.Muthusamy S. Tetrahedron 2002, 58: 9477 -
1i
Tietze LF.Modi A. Med. Res. Rev. 2000, 20: 304 -
1j
Tejedor D.Gonzalez-Cruz D.Santos-Exposito A.Marrero-Tellado JJ.de Armas P.Garcia-Tellado F. Chem. Eur. J. 2005, 11: 3502 -
1k
Lee JM.Na Y.Han H.Chang S. Chem. Soc. Rev. 2004, 33: 302 -
1l
Bunce RA. Tetrahedron 1995, 51: 13103 -
1m
Tietze LF.Rackelmann N. Pure Appl. Chem. 2004, 76: 1967 -
1n
Capdevila E.Rayo J.Carrion F.Jove I.Borrell JI.Teixido J. Afinidad 2003, 60: 317 - 2
Tietze LF. Chem. Rev. 1996, 96: 115 - 3
Mayer SF.Kroutil W.Faber K. Chem. Soc. Rev. 2001, 30: 332 - 4
Fogg DE.dos Santos EN. Coord. Chem. Rev. 2004, 248: 2365 -
5a
Hayashi T. Synlett 2001, 879 -
5b
Hayashi T.Yamasaki K. Chem. Rev. 2003, 103: 2829 -
5c
Fagnou K.Lautens M. Chem. Rev. 2003, 103: 169 - 6
Hayashi T.Senda T.Ogasawara M. J. Am. Chem. Soc. 2000, 122: 10716 - 7
Reetz MT.Moulin D.Gosberg A. Org. Lett. 2001, 3: 4083 - 8
Chapman CJ.Wadsworth KJ.Frost CG. J. Organomet. Chem. 2003, 680: 206 - 9
Chapman CJ.Frost CG. Adv. Synth. Catal. 2003, 345: 353 - 10
Navarre L.Darses S.Genêt JP. Angew. Chem. Int. Ed. 2004, 43: 719 - 11
Moss RJ.Wadsworth KJ.Chapman CJ.Frost CG. Chem. Commun. 2004, 1984 - 12
Takaya Y.Ogasawara M.Hayashi T.Sakai M.Miyaura N. J. Am. Chem. Soc. 1998, 120: 5579 - 13
Hargrave JD.Herbert J.Bish G.Frost CG. Org. Biomol. Chem. 2006, 4: 3235 - 14
Wadsworth KJ.Wood FK.Chapman CJ.Frost CG. Synlett 2004, 2022 - 15
Sibi MP.Tatamidani H.Patil K. Org. Lett. 2005, 7: 2571 - 16
Nishimura T.Hirabayashi S.Yasuhara Y.Hayashi T. J. Am. Chem. Soc. 2006, 128: 2556 - 17
Shintani R.Duan WL.Hayashi T. J. Am. Chem. Soc. 2006, 128: 5628 - 18
Hamashima Y.Somei H.Shimura Y.Tamura T.Sodeoka M. Org. Lett. 2004, 6: 1861 - 19
Kitamura M.Miki T.Nakano K.Noyori R. Tetrahedron Lett. 1996, 37: 5141 - 20
Yamada K.Arai T.Sasai H.Shibasaki M. J. Org. Chem. 1998, 63: 3666 - 21
Yoshida K.Ogasawara M.Hayashi T. J. Am. Chem. Soc. 2002, 124: 10984 - 22
Yoshida K.Ogasawara M.Hayashi T. J. Org. Chem. 2003, 68: 1901 - 23
Cauble DF.Gipson JD.Krische MJ. J. Am. Chem. Soc. 2003, 125: 1110 - 24
Bocknack BM.Wang LC.Krische MJ. Proc. Natl. Acad. Sci. U.S.A. 2004, 101: 5421 - 25
van Lingen HL.Zhuang W.Hansen T.Rutjes F.Jørgensen KA. Org. Biomol. Chem. 2003, 1: 1953 - 26
Guo RW.Morris RH.Song D. J. Am. Chem. Soc. 2005, 127: 516 - 27
Ikeda S.Cui DM.Sato Y. J. Am. Chem. Soc. 1999, 121: 4712 -
28a
Teoh E.Campi EM.Jackson WR.Robinson AJ. Chem. Commun. 2002, 978 -
28b
Teoh E.Campi EM.Jackson WR.Robinson AJ. New J. Chem. 2003, 27: 387 - 29
Teoh E.Jackson WR.Robinson AJ. Aust. J. Chem. 2005, 58: 63 - 30
Carpenter NE.Kucera DJ.Overman LE. J. Org. Chem. 1989, 54: 5846 - 31
Maddaford SP.Andersen NG.Cristofoli WA.Keay BA. J. Am. Chem. Soc. 1996, 118: 10766 - 32
Miyazaki F.Uotsu K.Shibasaki M. Tetrahedron 1998, 54: 13073 - 33
Lau SYW.Keay BA. Synlett 1999, 605 -
34a
Kojima A.Takemoto T.Sodeoka M.Shibasaki M. J. Org. Chem. 1996, 61: 4876 -
34b
Kojima A.Takemoto T.Sodeoka M.Shibasaki M. Synthesis 1998, 581 -
35a
Kagechika K.Ohshima T.Shibasaki M. Tetrahedron 1993, 49: 1773 -
35b
Ohshima T.Kagechika K.Adachi M.Sodeoka M.Shibasaki M. J. Am. Chem. Soc. 1996, 118: 7108 - 36
Flubacher D.Helmchen G. Tetrahedron Lett. 1999, 40: 3867 - 37
Brase S. Synlett 1999, 1654 - 38
Tietze LF.Sommer KM.Zinngrebe J.Stecker F. Angew. Chem. Int. Ed. 2005, 44: 257 -
39a
Choudary BM.Chowdari NS.Madhi S.Kantam ML. Angew. Chem. Int. Ed. 2001, 40: 4619 -
39b
Choudary BM.Chowdari NS.Madhi S.Kantam ML. J. Org. Chem. 2003, 68: 1736 - 40
Uozumi Y.Tanahashi A.Hayashi T. J. Org. Chem. 1993, 58: 6826 -
41a
Massacret M.Goux C.Lhoste P.Sinou D. Tetrahedron Lett. 1994, 35: 6093 -
41b
Massacret M.Lakhmiri R.Lhoste P.Nguefack C.Ben Abdelouahab FB.Fadel R.Sinou D. Tetrahedron: Asymmetry 2000, 11: 3561 - 42
Yamazaki A.Achiwa K. Tetrahedron: Asymmetry 1995, 6: 1021 - 43
Ito K.Imahayashi Y.Kuroda T.Eno S.Saito B.Katsuki T. Tetrahedron Lett. 2004, 45: 7277 - 44
Stragies R.Blechert S. J. Am. Chem. Soc. 2000, 122: 9584 - 45
Kaneko S.Yoshino T.Katoh T.Terashima S. Tetrahedron 1998, 54: 5471 -
46a
Du HF.Ding KL. Org. Lett. 2003, 5: 1091 -
46b
Du HF.Zhang X.Wang Z.Ding KL. Tetrahedron 2005, 61: 9465 - 47
Kaden S.Hiersemann M. Synlett 2002, 1999 - 48
Doyle MP.Forbes DC. Chem. Rev. 1998, 98: 911 - 49
Padwa A.Weingarten MD. Chem. Rev. 1996, 96: 223 -
50a
Gothelf KV.Jørgensen KA. Chem. Rev. 1998, 98: 863 -
50b
Padwa A. Acc. Chem. Res. 1991, 24: 22 - 51
Hodgson DM.Stupple PA.Johnstone C. Tetrahedron Lett. 1997, 38: 6471 -
52a
Hodgson DM.Stupple PA.Johnstone C. Chem. Commun. 1999, 2185 -
52b
Hodgson DM.Stupple PA.Pierard F.Labande AH.Johnstone C. Chem. Eur. J. 2001, 7: 4465 - 53
Hodgson DM.Selden DA.Dossetter AG. Tetrahedron: Asymmetry 2003, 14: 3841 -
54a
Hodgson DM.Labande AH.Pierard F. Synlett 2003, 59 -
54b
Hodgson DM.Labande AH.Pierard F.Castro MAE. J. Org. Chem. 2003, 68: 6153 - 55
Suga H.Ishida H.Ibata T. Tetrahedron Lett. 1998, 39: 3165 - 56
Kitagaki S.Anada M.Kataoka O.Matsuno K.Umeda C.Watanabe N.Hashimoto S. J. Am. Chem. Soc. 1999, 121: 1417 - 57
Kitagaki S.Yasugahira M.Anada M.Nakajima M.Hashimoto S. Tetrahedron Lett. 2000, 41: 5931 -
58a
Hodgson DM.Glen R.Grant GH.Redgrave AJ. J. Org. Chem. 2003, 68: 581 -
58b
Hodgson DM.Labande AH.Glen R.Redgrave AJ. Tetrahedron: Asymmetry 2003, 14: 921 - 59
Hodgson DM.Le Strat F.Avery TD.Donohue AC.Bruckl T. J. Org. Chem. 2004, 69: 8796 - 60
Shintani R.Fu GC. Angew. Chem. Int. Ed. 2003, 42: 4082 - 61
Murakami M.Katsuki T. Tetrahedron Lett. 2002, 43: 3947 - 62
Mikami K.Yajima T.Siree N.Terada M.Suzuki Y.Takanishi Y.Takezoe H. Synlett 1999, 1895 -
63a
Aboulhoda SJ.Reiners I.Wilken J.Henin F.Martens J.Muzart J. Tetrahedron: Asymmetry 1998, 9: 1847 -
63b
Muzart J.Henin F.Aboulhoda SJ. Tetrahedron: Asymmetry 1997, 8: 381 -
63c
Roy O.Diekmann M.Riahi A.Henin F.Muzart J. Chem. Commun. 2001, 533 -
63d
Roy O.Loiseau F.Riahi A.Henin F.Muzart J. Tetrahedron 2003, 59: 9641 - 64
Doi T.Kokubo M.Yamamoto K.Takahashi T. J. Org. Chem. 1998, 63: 428 - 65
Tian J.Yamagiwa N.Matsunaga S.Shibasaki M. Angew. Chem. Int. Ed. 2002, 41: 3636 - 66
Sasai H.Hiroi M.Yamada YMA.Shibasaki M. Tetrahedron Lett. 1997, 38: 6031 - 67
Taylor SJ.Duffey MO.Morken JP. J. Am. Chem. Soc. 2000, 122: 4528 - 68
Zhao CX.Duffey MO.Taylor SJ.Morken JP. Org. Lett. 2001, 3: 1829 - 69
Mikami K.Matsukawa S.Nagashima M.Funabashi H.Morishima H. Tetrahedron Lett. 1997, 38: 579 - 70
Bode SE.Wolberg M.Muller M. Synthesis 2006, 557 - 71
Mascarenhas CM.Miller SP.White PS.Morken JP. Angew. Chem. Int. Ed. 2001, 40: 601 - 72
Gnanadesikan V.Horiuchi Y.Ohshima T.Shibasaki M. J. Am. Chem. Soc. 2004, 126: 7782 - 73
Mlynarski J.Mitura M. Tetrahedron Lett. 2004, 45: 7549 -
74a
Schneider C.Hansch M. Chem. Commun. 2001, 1218 -
74b
Schneider C.Hansch M.Weide T. Chem. Eur. J. 2005, 11: 3010 -
74c
Schneider C.Klapa K.Hansch M. Synlett 2005, 91 - 75
Schneider C.Hansch M. Synlett 2003, 837 -
76a
Simpura I.Nevalainen V. Angew. Chem. Int. Ed. 2000, 39: 3422 -
76b
Simpura I.Nevalainen V. Tetrahedron 2003, 59: 7535 -
77a
La DS.Ford JG.Sattely ES.Bonitatebus PJ.Schrock RR.Hoveyda AH. J. Am. Chem. Soc. 1999, 121: 11603 -
77b
La DS.Sattely ES.Ford JG.Schrock RR.Hoveyda AH. J. Am. Chem. Soc. 2001, 123: 7767 - 78
Cefalo DR.Kiely AF.Wuchrer M.Jamieson JY.Schrock RR.Hoveyda AH. J. Am. Chem. Soc. 2001, 123: 3139 - 79
Weatherhead GS.Ford JG.Alexanian EJ.Schrock RR.Hoveyda AH. J. Am. Chem. Soc. 2000, 122: 1828 - 80
Tsang WCP.Jernelius JA.Cortez GA.Weatherhead GS.Schrock RR.Hoveyda AH. J. Am. Chem. Soc. 2003, 125: 2591 - 81
Weatherhead GS.Cortez GA.Schrock RR.Hoveyda AH. Proc. Natl. Acad. Sci. U.S.A. 2004, 101: 5805 -
82a
Sakurada I.Yamasaki S.Gottlich R.Iida T.Kanai M.Shibasaki M. J. Am. Chem. Soc. 2000, 122: 1245 -
82b
Yamasaki S.Kanai M.Shibasaki M. J. Am. Chem. Soc. 2001, 123: 1256 - 83
Tosaki SY.Tsuji R.Ohshima T.Shibasaki M. J. Am. Chem. Soc. 2005, 127: 2147 -
84a
Arai MA.Kuraishi M.Arai T.Sasai H. J. Am. Chem. Soc. 2001, 123: 2907 -
84b
Arai MA.Shinohara T.Arai T.Sasai H. J. Synth. Org. Chem. Jpn. 2004, 62: 59 - 85
Son SU.Park KH.Seo H.Chung YK.Lee SG. Chem. Commun. 2001, 2440 - 86
Otomaru Y.Hayashi T. Tetrahedron: Asymmetry 2004, 15: 2647 -
87a
Colby EA.Jamison TF. J. Org. Chem. 2003, 68: 156 -
87b
Miller KM.Huang WS.Jamison TF. J. Am. Chem. Soc. 2003, 125: 3442 - 88
Miller KM.Colby EA.Woodin KS.Jamison TF. Adv. Synth. Catal. 2005, 347: 1533 - 89
Ng SS.Jamison TF. Tetrahedron 2005, 61: 11405 - 90
Pei T.Widenhoefer RA. J. Org. Chem. 2001, 66: 7639 - 91
Lei JG.Hong R.Yuan SG.Lin GQ. Synlett 2002, 927 - 92
de Alaniz JR.Rovis T. J. Am. Chem. Soc. 2005, 127: 6284 - 93
Wang Y.Liu XF.Deng L. J. Am. Chem. Soc. 2006, 128: 3928 - 94
Bui T.Barbas CF. Tetrahedron Lett. 2000, 41: 6951 - 95
Betancort JM.Sakthivel K.Thayumanavan R.Barbas CF. Tetrahedron Lett. 2001, 42: 4441 - 96
Huang Y.Walji AM.Larsen CH.MacMillan DWC. J. Am. Chem. Soc. 2005, 127: 15051 - 97
Enders D.Hüttl MRM.Grondal C.Raabe G. Nature 2006, 441: 861 - 98
Gryko D. Tetrahedron: Asymmetry 2005, 16: 1377 -
99a
Halland N.Aburel PS.Jørgensen KA. Angew. Chem. Int. Ed. 2004, 43: 1272 -
99b
Pulkkinen J.Aburel PS.Halland N.Jørgensen KA. Adv. Synth. Catal. 2004, 346: 1077 - 100
Hong B.-C.Wu M.-F.Tseng H.-C.Liao J.-H. Org. Lett. 2006, 8: 2217 - 101
Iwabuchi Y.Nakatani M.Yokoyama N.Hatakeyama S. J. Am. Chem. Soc. 1999, 121: 10219 - 102
Cordova A.Notz W.Barbas CF. J. Org. Chem. 2002, 67: 301 - 103
Chowdari NS.Ramachary DB.Cordova A.Barbas CF. Tetrahedron Lett. 2002, 43: 9591 - 104
Chowdari NS.Ramachary DB.Barbas CF. Org. Lett. 2003, 5: 1685 - 105
Yamamoto Y.Momiyama N.Yamamoto H. J. Am. Chem. Soc. 2004, 126: 5962 -
106a
List B. J. Am. Chem. Soc. 2000, 122: 9336 -
106b
List B.Pojarliev P.Biller WT.Martin HJ. J. Am. Chem. Soc. 2002, 124: 827 - 107
Notz W.Sakthivel K.Bui T.Zhong GF.Barbas CF. Tetrahedron Lett. 2001, 42: 199 - 108
Hayashi Y.Tsuboi W.Ashimine I.Urushima T.Shoji M.Sakai K. Angew. Chem. Int. Ed. 2003, 42: 3677 - 109
Cordova A. Synlett 2003, 1651 - 110
Ibrahem I.Casas J.Cordova A. Angew. Chem. Int. Ed. 2004, 43: 6528 - 111
Ramachary DB.Chowdari NS.Barbas CF. Angew. Chem. Int. Ed. 2003, 42: 4233 - 112
Ramachary DB.Barbas CF. Chem. Eur. J. 2004, 10: 5323 - 113
Calter MA.Guo X. J. Org. Chem. 1998, 63: 5308 - 114
Dudding T.Hafez AM.Taggi AE.Wagerle TR.Lectka T. Org. Lett. 2002, 4: 387 - 115
Hafez AM.Dudding T.Wagerle TR.Shah MH.Taggi AE.Lectka T. J. Org. Chem. 2003, 68: 5819 -
116a
France S.Shah MH.Weatherwax A.Wack H.Roth JP.Lectka T. J. Am. Chem. Soc. 2005, 127: 1206 -
116b
France S.Wack H.Hafez AM.Taggi AE.Witsil DR.Lectka T. Org. Lett. 2002, 4: 1603 - 117
France S.Wack H.Taggi AE.Hafez AM.Wagerle TR.Shah MH.Dusich CL.Lectka T. J. Am. Chem. Soc. 2004, 126: 4245